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[ CAS No. 808744-34-5 ] {[proInfo.proName]}

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Chemical Structure| 808744-34-5
Chemical Structure| 808744-34-5
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Quality Control of [ 808744-34-5 ]

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Product Details of [ 808744-34-5 ]

CAS No. :808744-34-5 MDL No. :MFCD07778353
Formula : C7H5BrN2 Boiling Point : No data available
Linear Structure Formula :- InChI Key :OASOJRLJBDCVNU-UHFFFAOYSA-N
M.W : 197.03 Pubchem ID :15098903
Synonyms :

Calculated chemistry of [ 808744-34-5 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 42.89
TPSA : 17.3 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.76 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.94
Log Po/w (XLOGP3) : 2.45
Log Po/w (WLOGP) : 2.1
Log Po/w (MLOGP) : 1.48
Log Po/w (SILICOS-IT) : 1.67
Consensus Log Po/w : 1.93

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.27
Solubility : 0.106 mg/ml ; 0.000536 mol/l
Class : Soluble
Log S (Ali) : -2.46
Solubility : 0.688 mg/ml ; 0.00349 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.94
Solubility : 0.225 mg/ml ; 0.00114 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.66

Safety of [ 808744-34-5 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P305+P351+P338 UN#:
Hazard Statements:H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 808744-34-5 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 808744-34-5 ]

[ 808744-34-5 ] Synthesis Path-Downstream   1~12

  • 2
  • [ 421-17-0 ]
  • [ 808744-34-5 ]
  • 3-trifluoromethylsulfanyl-5-bromoimidazol{1,2a}pyridine hydrochloride [ No CAS ]
  • 3
  • [ 808744-34-5 ]
  • [ 1692-25-7 ]
  • [ 1067914-66-2 ]
YieldReaction ConditionsOperation in experiment
75% With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In water; N,N-dimethyl-formamide; acetonitrile; at 60℃; for 18h; Step B: Preparation of 7-(pyridin-3-yl)imidazori.2-a1pyridine:; A suspension of potassium carbonate (0351 g, 2.54 mmol), pyridin-3-ylboronic acid (68.6 mg5 0.558 mmol), 7- bromoimidazo[l52-a]pyridine (0.100 g, 0.508 mmol) and tetrakis(triphenylphosphine) <n="70"/>palladium (0) (29.3 mg, 0.025 mmol) in 6.5 ml of a 1:1 :4.5 mixture of water:dimethylformamide:acetonitrile was degassed thoroughly under a nitrogen atmosphere, and heated at 60 0C for 18 hours. The reaction mixture was poured in water (50 ml) and extracted with dichloromethane and EtOAc. The combined organic extracts were dried over anhydrous sodium sulfate and concentrated to afford a solid. The solid was purified by silica gel chromatography (eluting with 6% MeOH-chloroform) to afford the desired compound (74.1 mg, 75 % yield). MS APCI (+) m/z 196.3 (M+l) detected.
75% With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In water; N,N-dimethyl-formamide; acetonitrile; at 60℃; for 18h; A suspension of potassium carbonate (0.351 g, 2.54 mmol), pyridine-3-ylboronic acid (68.6 mg, 0.558 mmol), 7-bromoimidazo[l,2-a] pyridine (0.100 g, 0.508 mmol) and tetrakis(triphenylphosphine) palladium (0) (29.3 mg, 0.025 mmol) in 6.5 ml of a 1:1 :4.5 mixture of water:dimethylformamide:acetonitrile was degassed thoroughly under a nitrogen atmosphere, and heated at 60 C for 18 hours. The reaction mixture was poured in water (50 ml) and extracted with dichloromethane and EtOAc. The combined organic extracts were dried over anhydrous sodium sulfate and concentrated to afford a solid. The solid was purified by silica gel chromatography (eluting with 6% MeOH-chloroform) to afford the desired compound (74.1 mg, 75 % yield). MS APCI (+) m/z 196.3 (M+l) detected.
  • 4
  • [ 107-20-0 ]
  • [ 84249-14-9 ]
  • [ 808744-34-5 ]
YieldReaction ConditionsOperation in experiment
100% In water; at 100℃; for 4h; To a suspension of 4-bromopyridin-2-amine (5.26 g, 30.40 mmol) in water (50 mL) was added 2-chloroacetaldehyde (40% [w/w] in water, 15.24 g, 77.66 mmol). The reaction mixture was stirred at 100 C for 4 h, and adjusted to pH = 10 with a saturated Na2CO, aqueous solution, then extracted with DCM (100 mL c 3). The combined organic phases were washed with brine (100 mL), dried over anhydrous Na2S04, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography (MeOH/DCM (v/v) = 1/100) to give the title compound as yellow oil (5.93 g, yield 100%).MS (ESI, pos. ion) m/z: 197.2 [M+H]+;1H NMR (400MHz, CDCl3) d (ppm): 8.00 (d, j = 7.2 Hz, 1H), 7.82 (d, J = 0.8 Hz, 1H), 7.61 (s, 1H), 7.57 (s, 1H), 6.90 (dd, j= 7.2, 1.7 Hz, 1H).
100% In water; at 100℃; for 4h; To 4-bromopyridin-2-amine (5.26 g, 30.40 mmol)In water (50mL) suspension2-chloroacetaldehyde (40% [w/w] in water, 15.24 g, 77.66 mmol).The reaction mixture was stirred at 100 C for 4 hours.After the reaction,Adjust to pH=10 with a saturated aqueous solution of sodium carbonate.It was then extracted with dichloromethane (100 mL x 3).The combined organic phases were washed with saturated brine (100 mL).Dry over anhydrous sodium sulfate,Filter and concentrate under reduced pressure.The residue obtained is purified by silica gel column chromatography (MeOH/DCM (v/v) = 1/100).The title compound was obtained as a yellow liquid (5.93 g, yield 100%).
78% With sodium hydrogencarbonate; In ethanol; for 6h;Reflux; The compound 2-amino-4-bromopyridine 22 (5.0 g) and 2-chloroacetaldehyde (40%solution, 12 mL, 2.5 eq) was dissolved in absolute ethanol (50 mL)After addition of NaHCO3 (4.89 g, 2.0 eq)Reflux reaction 6h.The organic solvent was removed by vacuum filtration, washed with EA (60 mL), washed with water, saturated with brine, dried over Na2SO4 and dried on a dry column to give brown solid 23 (4.38 g, 78%).
71% Example 44; 8-(ftrans)-3-fluoropiperidin-4-yloxy)-2-(7-(pyridin-3-yl)imidazo[1.2-a]pyridin-3-yl)qiotaiotainoluie; Step A: Preparation of 7-bromoimidazo[1.2-a]pyridine:; A solution of 4- bromopyridin-2-amine (1.00 g, 5.78 mmol) and 2-chloroacetaldehyde (50% wt aqueous solution, 1.83 ml5 14.45 mmol) in absolute ethanol (9.5 ml) was refluxed for 12 hours, and then allowed to cool to ambient temperature overnight. The reaction mixture was concentrated under reduced pressure and carefully re-suspended in saturated aqueous bicarbonate solution (100 ml). The resulting mixture was extracted thoroughly with DCM and EtOAc, and the combined organic extracts were dried over anhydrous sodium sulfate and concentrated to afford 1.31 g of a solid. The solid was purified by silica gel chromatography (eluting with 3% MeOH-chloroform) to afford the desired compound (0.808 g5 71 % yield). MS APCI (+) m/z 197.1 and 199.1 (M+l for each isotope) detected.
71% In ethanol; water; at 20℃; for 12h;Heating / reflux; A solution of 4- bromopyridin-2-amine (1.00 g, 5.78 mmol) and 2-chloroacetaldehyde (50% wt aqueous solution, 1.83 ml, 14.45 mmol) in absolute ethanol (9.5 ml) was refluxed for 12 hours, and then allowed to cool to ambient temperature overnight. The reaction mixture was concentrated under reduced pressure and carefully re-suspended in saturated aqueous bicarbonate solution (100 ml). The resulting mixture was extracted thoroughly with DCM and EtOAc, and the combined organic extracts were dried over anhydrous sodium sulfate and concentrated to afford 1.31 g of a solid. The solid was purified by silica gel chromatography (eluting with 3% MeOH-chloroform) to afford the desired compound (0.808 g, 71 % yield). MS APCI (+) m/z 197.1 and 199.1 (M+l for each isotope) detected.
63% With sodium hydrogencarbonate; In ethanol; for 16h;Reflux; To a stirred solution of 4-bromopyridin-2-amine (5 g, 28.9 mmol, Molekula Biokem Ltd) in EtCH (5OmL), added sodium bicarbonate (7.28 g, 86.7 mmol) and chloroacetaldehyde (5 mL, 115 mmol) and refluxed for 16 h. The reaction mixture was evaporated under vacuum and water (25 mL) was added to the crude mixture. The resulting solution was extractedwith EtOAc (2 x 50 mL). The organic layer was dried over anhydrous Na2SO4 and concentrated. The resulting crude product was purified by flash chromatography. Yield:63% (3.6 g, brown solid). LCMS: (Method B) 199.0 (M +H), Rt. 3.92 mm, 94.50% (Max).
63% With sodium hydrogencarbonate; In ethanol; for 16h;Reflux; To a stirred solution of 4-bromopyridin-2-amine (5 g, 28.9 mmol, Molekula Biokem Ltd) in EtOH (50ml_), added sodium bicarbonate (7.28 g, 86.7 mmol) and chloroacetaldehyde (5 mL, 1 15 mmol) and refluxed for 16 h. The reaction mixture was evaporated under vacuum and water (25 mL) was added to the crude mixture. The resulting solution was extracted with EtOAc (2 x 50 mL). The organic layer was dried over anhydrous Na2SO4 and concentrated. The resulting crude product was purified by flash chromatography. Yield: 63% (3.6 g, brown solid). LCMS: (Method B) 199.0 (M +H), Rt. 3.92 min, 94.50% (Max).
With sodium hydrogencarbonate; In ethanol; for 17h;Heating / reflux; 4-Bromo-pyridin-2-ylamine (1 eq, 5.78 mmol, 1 g) is added to a solution of chloroacetic aldehyde (5 eq, 28.9 mmol, 5 ml) in EtOH (25 ml). NaHCO3 (2 eq, 11.6 mmol, 971 g) is then added and the reaction mixture is heated at reflux for 17 h. The solvent is then removed in vacuo and the product is purified by flash column chromatography eluting with 9:1 DCM/MeOH to afford 7-bromo-imidazo-[1,2-a]- pyridine as a brown solid; [M+H]+ = 198
INTERMEDIATE SYNTHESIS; 7-bromo-3-iodoimidazo[ 1 ,2-a]pyridine; (1) 7-bromoimidazo[l,2-a]pyridine.; To a 100 niL round -bottomed flask was added 4-bromopyridin-2-amine (4.0 g, 23.1 mmol), chloroacetaldehyde, 50% in water (14.9 rnL, 116 mmol), and EtOH (25 mL). The resulting reaction mixture was heated at 100 0C under N2 for 3 h. The reaction was cooled to rt and the solvent was concentrated. The residue was redissolved in EtOAc. The organic layer was washed with sat. NaHCObeta (2 x 40 mL), water (2 x 40 mL), brine, dried over MgSO4, and removed solvent. The crude product was purified using SiO2 chromatography (Teledyne Isco RediSep, 12O g SiO2, DCM:MeOH=96%:4% to DCM:MeOH (2M NH3)=95%:5%, Flow = 85 niL/min). The solvent was removed in vacuo to afford the desired product as brown solid (3.8 g). MS (ESI pos. ion) m/z: 196.8. Calcd exact mass for C7H5BrN2: 195.9. 1U NMR (300 MHz, CHLOROFORM-J) delta ppm 6.90 (d, J=7.16 Hz, 1 H) 7.57 (s, 1 H) 7.62 (s, 1 H) 7.83 (s, 1 H) 8.00 (d, J=7.16 Hz, 1 H).
18.6 g In ethanol; water; at 0℃;Reflux; The compound 2-amino-4-bromopyridine 6 (20.00 g, 116.28 mmol) was dissolved in a mixture of ethanol (300 mL) and water (30 mL).After stirring for 20 minutes under ice bath conditions, when the solution temperature drops to 0 C,40% chloroacetaldehyde (28.60 mL, 174.40 mmol) was added slowly and stirred at reflux overnight.The mixture was filtered with Celite, and then evaporated and evaporated.Washed with water, washed with saturated brine, dried with Na2SO4 and then driedColumn chromatography gave a brown solid 8 (18.60 g, 81%).

  • 5
  • [ 808744-34-5 ]
  • [ 17997-47-6 ]
  • [ 908267-70-9 ]
YieldReaction ConditionsOperation in experiment
39% With triethylamine;tris-(dibenzylideneacetone)dipalladium(0); tris-(o-tolyl)phosphine; In N,N-dimethyl-formamide; at 100℃; for 17h; A solution of7-bromoimidazo[l,2-a]pyridine (0.100 g, 0.508 mmol), tri-o-tolylphosphine, tris(dibenzylideneacetone)dipalladium(0) (47 mg, 0.051 mmol), and 2-tri-n- butylstannylpyridine (0.234 g, 0.508 mmol) in anhydrous DMF (5 ml) was combined at ambient temperature under a nitrogen atmosphere with triethylamine (65 mg, 0.65 mmol). The reaction mixture was heated at 100 0C for 17 hours. The reaction mixture was then allowed to cool, poured in water (40 ml), and extracted with DCM, ether, and EtOAc. The combined organic extracts were dried over anhydrous sodium sulfate and concentrated to afford a solid. The solid was purified by silica gel chromatography (eluting with 5% MeOH-DCM) to afford the desired compound (38.4 mg, 39% yield). MS APCI (+) m/z 196.3 (M+l) detected
  • 6
  • [ 808744-34-5 ]
  • [ 847818-74-0 ]
  • [ 1036761-86-0 ]
YieldReaction ConditionsOperation in experiment
70% With potassium carbonate;bis(tri-t-butylphosphine)palladium(0); In ethanol; water; toluene; at 75℃; for 2h; Procedure B1c - Suzuki coupling for heterocvcles.; A solution of 7-Bromo-imidazol[1 ,2-a]pyridine (0.5g, 2.54mmol, 1 equivalent, made according to general procedure A1 using 4-bromo-pyridin-2-ylamine instead of 4-chloro-pyridin-2- ylamine) , 1 -methyl-5-(4,4, 5, 5-tetramethyl-[ 1 , 3, 2]dioxaborolan-2-yl)- 1 H-py razole ( 1.1 g, 5.08mmol, 2 equivalents), bis(tri-t-butylphosphine) palladium (0) (66mg, 0.13mmol, 0.05 equivalents) and potassium carbonate (2.1g, 15.24mmol, 6 equivalents) in ethanol (10ml), toluene (10ml) and water (10ml) was heated at 750C for 2 hours. The reaction mixture was partitioned between ethyl acetate and water. The organic layer was then washed with a saturated brine solution, dried (MgSO4), filtered and the solvent removed by evaporation in vacuo. The residue was purified by column chromatography (Biotage SP4, 25S, flow rate 25ml/min, gradient 0% to 20% methanol in ethyl acetate) to give 7-(2-methyl-2H-pyrazol-3-yl)- imidazo[1 ,2,a]pyridine as a colourless oil (350mg, 70%). MS: [M+H]+ 199.
  • 7
  • 3-(methylcarbamoyl)phenylboronic acid [ No CAS ]
  • [ 808744-34-5 ]
  • [ 1146615-82-8 ]
YieldReaction ConditionsOperation in experiment
With sodium carbonate;bis-triphenylphosphine-palladium(II) chloride; In 1,2-dimethoxyethane; water; at 120℃; for 0.166667h;Microwave radiation; 7-Bromo-imidazo-[1,2-a]-pyridine (1 eq, 0.5 mmol, 100 mg) and (3-methylamino carbonylphenyl)boronic acid (1.1 eq, 0.558 mmol, 99.9 mg) are dissolved in DME (3 ml) and water (0.8 ml) and Na2CO3 (3 eq, 1.52 mmol, 161 mg) is added. PdCl2(PPh3)I (0.05 eq, 0.025 mmol, 17.8 mg) is then added and the reaction mixture is heated using microwave radiation at 120C for 10 min. At the completion of this time the solvent is removed in vacuo and the reaction mixture is purified by flash column chromatography eluting with 9:1 DCM/MeOH to yield 3-imidazo[1,2-a]pyridine-7-yl- N-methyl-benzamide as a brown solid; [M+H]+ = 252
  • 8
  • [ 808744-34-5 ]
  • [ 1246184-55-3 ]
YieldReaction ConditionsOperation in experiment
86.9% With N-iodo-succinimide; In N,N-dimethyl-formamide; at 100℃; for 1h; To a solution of 7-bromoimidazo[l,2-a]pyridine (5.93 g, 30.1 mmol) in DMF (60 mL) was added NIS (9.19 g, 40.8 mmol). The reaction mixture was stirred at 100 C for 1 hour, then cooled down to rt and quenched with water (50 mL), then extracted with DCM (100 mL x 3). The combined organic phases were washed with brine (100 mL), dried over anhydrous Na2S04, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/PE (v/v) = 1/10) to give the title compound as a yellow solid (8.45 g, yield 86.9%).MS (ESI, pos. ion) m/z: 323.0 [M+H]+;1H NMR (400 MHz, CDCl3) d (ppm): 8.02 (d, J= 7.3 Hz, 1H), 7.83 (d, J= 1.2 Hz, 1H), 7.69 (s, 1H), 7.05 (dd, j= 7.3, 1.7 Hz, 1H).
86.9% With N-iodo-succinimide; In N,N-dimethyl-formamide; at 100℃; for 1h; To <strong>[808744-34-5]7-bromoimidazo[1,2-a]pyridine</strong> (5.93 g, 30.1 mmol)Add in DMF (60mL) solutionNIS (9.19 g, 40.8 mmol).The reaction mixture was stirred at 100 C for 1 hour.Then cool to room temperature,The reaction was quenched by the addition of water (50 mL).It was then extracted with DCM (100 mL x 3).Combined organic phase with saturated brine (100 mL)Washed, dried over anhydrous sodium sulfate,Filter and concentrate under reduced pressure.The residue obtained was purified by silica gel column chromatography (EtOAc /EtOAcThe title compound was obtained as a white solid (8.45 g, yield 86.9%).
With iodine; sodium acetate; In methanol; at 0℃; (2) 7-bromo-3-iodoimidazo[l,2-a]pyridine.; To a 250 mL round bottomed flask was added 7-bromoimidazo[l,2-a]pyridine (3.8 g, 19.29 mmol), sodium acetate (4.3 g, 52.1 mmol) and MeOH (60 mL). The resulting mixture was cooled to 0 0C followed by adding diiodine (8.3 g, 32.8 mmol). After the addition, ice bath was removed and the mixture was continued to stir for 5 h. The solvent was concentrated. The crude product was purified using SiO2 chromatography (Teledyne Isco RediSep, 330 g SiO2, hexanes:acetone= 80%:20%, Flow = 100 mL/min). The solvent was removed in vacuo to afford the desired product as light yellow solid (3.2 g). (ESI pos. ion) m/z: 322.8. Calcd exact mass for C7H4BrIN2: 321.9. 1H NMR (300 MHz, CHLOROFORM-^) delta ppm 7.04 (d, J=7.02 Hz, 1 H) 7.68 (s, 1 H) 7.82 (s, 1 H) 8.01 (d, J=7.31 Hz, I H).
  • 9
  • [ 808744-34-5 ]
  • [ 1276022-88-8 ]
  • [ 1276023-79-0 ]
YieldReaction ConditionsOperation in experiment
58.4% With rac-diaminocyclohexane; cesium fluoride;copper(l) iodide; In 1,4-dioxane; at 95℃;Inert atmosphere; 1 equiv. of the oxazolidin-2-one was given together with <strong>[808744-34-5]7-bromoimidazo[1,2-a]pyridine</strong> (1 equiv.), cesium fluoride (2 equiv.) and copper(I) iodide (0.1 equiv.) in a flask. The flask was purged with argon and a solution of cyclohexane-1,2-diamine (0.1 equiv.) in dioxane was added. The reaction was stirred at 95 C. until TLC indicated consumption of the oxazolidin-2-one. After cooling to 45 C. the reaction mixture was filtered through a pad of CELITE, the pad was washed with warm dichloromethane and the solution was concentrated under reduced pressure. The final product was purified via FPLC using a chloroform-methanol gradient (0?10%). Step D:Product obtained from step C (0.376 g, 1.7 mmol), <strong>[808744-34-5]7-bromoimidazo[1,2-a]pyridine</strong> (0.335 g, 1.7 mmol), copper(I) iodide (0.033 g, 0.17 mmol), cesium fluoride (0.52 g, 3.4 mmol), cyclohexane-1,2-diamine (0.021 mL, 0.17 mmol), yield: 0.335 g (58.4%)Overall yield: 8.7%; MS m/z 338.2 (M+H)+; 1H NMR (400 MHz, DMSO-D6): delta 0.92 (t, 3H, J=7.5 Hz); 1.62-1.70 (m, 2H); 3.83-3.87 (m, 2H); 4.12-4.16 (m, H); 4.80-4.84 (m, H); 5.71-5.74 (m, H); 6.89 (d, 2H, J=8.7); 7.26 (d, H, J=7.5 Hz); 7.31-7.38 (m, 3H); 7.48 (br s, H); 7.83 (br s, H); 8.46 (br s, H), HPLC (lambda=214 nm), [B]: rt 11.20 min (95%).
  • 10
  • [ 808744-34-5 ]
  • [ 1276023-75-6 ]
  • [ 1276023-83-6 ]
YieldReaction ConditionsOperation in experiment
31.3% With potassium carbonate; rac-diaminocyclohexane;copper(l) iodide; In 1,4-dioxane; at 95℃;Inert atmosphere; 1 equiv. of the 1,3-oxazinan-2-one was given together with <strong>[808744-34-5]7-bromoimidazo[1,2-a]pyridine</strong> (1 equiv.), potassium carbonate (2 equiv.) and copper(I) iodide (0.1 equiv.) in a flask. The flask was purged with argon and a solution of cyclohexane-1,2-diamine (0.1 equiv.) in dioxane was added. The reaction was stirred at 95 C. until TLC indicated consumption of the 1,3-oxazinan-2-one. After cooling to 45 C. the reaction mixture was filtered through a pad of CELITE, the pad was washed with warm dichloromethane and the solution was concentrated under reduced pressure. The final product was purified via FPLC using a chloroform-methanol gradient (0?10%). Step D:Product obtained from step C (0.45 g, 1.91 mmol), <strong>[808744-34-5]7-bromoimidazo[1,2-a]pyridine</strong> (0.376 g, 1.91 mmol), copper(I) iodide (0.036 g, 0.19 mmol), potassium carbonate (0.528 g, 3.82 mmol), cyclohexane-1,2-diamine (0.023 mL, 0.19 mmol), yield: 0.210 g (31.3%)Overall yield: 6.1%; MS m/z 352.3 (M+H)+; 1H-NMR (400 MHz, DMSO-d6): delta 0.87-0.91 (m, 3H); 1.58-1.67 (m, 2H); 2.05-2.12 (m, H); 2.49-2.57 (m, H); 3.79-3.82 (m, 2H); 4.20-4.26 (m, H); 4.35-4.40 (m, H); 5.45-5.47 (m, H); 6.81 (d, 2H, J=8.7 Hz); 7.24 (d, 2H, J=8.7 Hz); 7.47 (d, H, J=7.9 Hz); 7.75 (s, H); 7.96 (s, H); 8.10 (s, H); 8.65 (d, H, J=7.9 Hz), HPLC (lambda=214 nm), [B]: rt 9.73 min (100%).
  • 11
  • [ 808744-34-5 ]
  • 3-(4-bromophenyl)-4-[(3S)-1-(cyclopropylcarbonyl)-3-pyrrolidinyl]methyl}-4H-1,2,4-triazole [ No CAS ]
  • 7-[4-(4-[(3S)-1-(cyclopropylcarbonyl)-3-pyrrolidinyl]methyl}-4H-1,2,4-triazol-3-yl)phenyl]imidazo[1,2-a]pyridin [ No CAS ]
YieldReaction ConditionsOperation in experiment
13% Example 687-[4-(4- [(35)- 1 -(cyclopropylcarbonyl)-3-pyrrolidinyl]methyl} -4H- 1 ,2,4-triazol-3- yl)phenyl]imidazo[ 1 ,2-a]pyridinA mixture of 7-bromoimidazo[l,2-a]pyridine (125 mg, 0.634 mmol),￡zs(pinacolato)diboron (180 mg, 0.709 mmol), KOAc (250 mg, 2.55 mmol), andPdCl2(dppf) (50 mg, 0.061 mmol) in 1,4-dioxane (3 mL) was stirred at 100 C. 3-(4- Bromophenyl)-4- { [(35)- 1 -(cyclopropylcarbonyl)-3-pyrrolidinyl]methyl} -4H- 1 ,2,4-triazole (230 mg, 0.613 mmol) and 2 M aq. K2C03 (1.5 mL) were added and the reaction mixture was stirred at 100 C overnight. The 1,4-dioxane layer was removed, passed through a plug of Celite and Na2S04, rinsed with 1,4-dioxane (4 mL), and the organic layers concentrated in vacuo. Purification of the residue by reverse phase HPLC (5-45%CH3CN/water with 0.1% TFA), reverse phase HPLC (10-70% CH3CN/water with 0.1% NH4OH), and then reverse phase HPLC (2-40% MeOH/water with 0.08% NH4OH) provided the title compound (36 mg, 13%). MS(ES)+ m/e 413.3 [M+H]+.
  • 12
  • [ 808744-34-5 ]
  • 1-[1-(cyclopropylcarbonyl)-3-pyrrolidinyl]methyl}-2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-5-(trifluoromethyl)-1H-benzimidazole [ No CAS ]
  • 1-[1-(cyclopropylcarbonyl)-3-pyrrolidinyl]methyl}-2-(4-imidazo[1,2-a]pyridin-7-ylphenyl)-5-(trifluoromethyl)-1H-benzimidazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In 1,4-dioxane; water; at 100℃; for 2h;Inert atmosphere; Sealed vial; Example 145l-[(3S)-l-(Cyclopropylcarbonyl)-3-pyrrolidinyl]methyl}-2-(4-imidazo[l,2-fl]pyridin- 7-ylphenyl)-5-(trifluoromethyl)-lH-benzimidazole2-(4-Bromophenyl)- 1 - { [(3 S)- 1 -(cyclopropylcarbonyl)-3-pyrrolidinyl]methyl} -5- (trifluoromethyl)-lH-benzimidazole (82 mg, 0.167 mmol) was dissolved in 1,4-dioxane (1.5 mL) in 5-mL microwave vial. Potassium acetate (44.8 mg, 0.457 mmol),4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi-l,3,2-dioxaborolane (42.5 mg, 0.167 mmol), andPdCl2(dppf)-CH2Cl2 adduct (6.22 mg, 7.61 umol) were then added with stirring. The vial was purged with nitrogen, sealed, and heated to 100 C for 2 hours. The reaction mixture was allowed to cool to room temperature. 7-Bromoimidazo[l,2-a]pyridine (30 mg, 0.152 mmol), PdCl2(dppf)-CH2Cl2 adduct (6.22 mg, 7.61 umol) and 2 M aqueous potassium carbonate (0.228 mL, 0.457 mmol) were then added. The vial was again purged with nitrogen, sealed and heated at 100 C for 2 hours. The reaction mixture was allowed to cool to room temperature, diluted with water (50 mL), acidified to pH 7 with 1 N HC1, and extracted with DCM (3 x 50 mL). The combined DCM extracts were dried over sodium sulfate and evaporated to dryness. The resulting crude product was dissolved in DMSO and purified by preparative reverse phase hplc. The appropriate fractions were combined and the pH adjusted to 7 with aqueous sodium bicarbonate (saturated) and extracted with DCM (3 x 25 mL). The combined DCM extracts were dried over sodium sulfate and evaporated to dryness to afford 22 mg of the titled compound. (LCMS m/z 529.9, M+H).
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