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[ CAS No. 76041-73-1 ] {[proInfo.proName]}

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Chemical Structure| 76041-73-1
Chemical Structure| 76041-73-1
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Quality Control of [ 76041-73-1 ]

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Product Details of [ 76041-73-1 ]

CAS No. :76041-73-1 MDL No. :MFCD02691223
Formula : C6H3BrF3NO Boiling Point : -
Linear Structure Formula :- InChI Key :UWHKLLYQUQPOQK-UHFFFAOYSA-N
M.W : 241.99 Pubchem ID :13491775
Synonyms :

Calculated chemistry of [ 76041-73-1 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.17
Num. rotatable bonds : 1
Num. H-bond acceptors : 5.0
Num. H-bond donors : 1.0
Molar Refractivity : 38.96
TPSA : 33.12 ?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) : -6.07 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.83
Log Po/w (XLOGP3) : 2.41
Log Po/w (WLOGP) : 3.72
Log Po/w (MLOGP) : 2.08
Log Po/w (SILICOS-IT) : 2.6
Consensus Log Po/w : 2.53

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.16
Solubility : 0.166 mg/ml ; 0.000688 mol/l
Class : Soluble
Log S (Ali) : -2.75
Solubility : 0.433 mg/ml ; 0.00179 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.19
Solubility : 0.154 mg/ml ; 0.000638 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.86

Safety of [ 76041-73-1 ]

Signal Word:Warning Class:
Precautionary Statements:P280-P305+P351+P338 UN#:
Hazard Statements:H317-H319 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 76041-73-1 ]

* 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 [ 76041-73-1 ]

[ 76041-73-1 ] Synthesis Path-Downstream   1~7

  • 1
  • [ 33252-63-0 ]
  • [ 76041-73-1 ]
YieldReaction ConditionsOperation in experiment
99.8% To a solution of 5-(trifluoromethyl)pyridin-2-ol (10.52 g, 62 mmol) and sodium acetate (5.29 g, 64 mmol) in glacial acetic acid (38 mL) was added bromine (3.36 mL, 65 mmol) at room temperature. The white cloudy solution slowly turned into a clear brown solution, which was heated at 80 C. for 2.5 h. The mixture was allowed to cool to room temperature and then evaporated under reduced pressure. The residue was neutralized with saturated NaHCO3 solution to pH=8. The resulting solution was extracted with EtOAc three times. The combined extracts were dried over MgSO4, filtered, and evaporated in vacuo to yield 15.1 g (99.8%) of the crude product (15.1 g, 98.8%) as a white solid. LC-MS calculated for C6H3BrF3NO: (M+H)+241.9; found 241.9/243.9. Step A-2
98% With bromine; sodium acetate; In acetic acid; at 80℃; for 2.5h; To a solution of 5-trifluoromethyl-2-pyridinal (51 g, 310 mmol) and sodium acetate (26. 2G, 319 mmol) in glacial acetic acid (200 mL) was added bromine (16.7 ML, 325 mmol) and the resulting mixture was heated at 80 C for 2.5 h. The reaction was allow to cool to room temperature and then was evaporated under reduced pressure. The residue was neutralized with saturated NaHC03 solution and extracted with ethyl acetate (3 x 200 mL). The organics were combined, dried over MGS04, filtered, and evaporated in vacuo to yield 74.45 g (98%) of the crude product. 1H NMR (400 MHz, CDC13) 8 8.04 (d, J=2.6 Hz, 1H), 7.89 (m, 1H).
98.7% With bromine; sodium acetate; In acetic acid; at 80℃; for 2.5h; To a solution of 5-TRIFLUOROMETHYL-2-PYRIDINOL (51. 0 g, 307 mmol) and sodium acetate (26.2 g, 319 mmol) in glacial acetic acid (200 mL) was added bromine (16.7 mL, 325 mmol) and the resulting mixture was heated at 80 C for 2.5 hours. The reaction was allow to cool to room temperature and then was evaporated under reduced pressure. The residue was neutralized with saturated NAHC03 solution and extracted with ethyl acetate (3 x 200 mL). The organic layers were combined, dried over MgS04, filtered, and evaporated in vacuo to yield 74.45 g (98.7%) of the crude PRODUCT. H NMR (400 MHz, CD) 5 8.04 (d, J=2.6 Hz, 1H), 7.89 (m, 1H).
98.7% INTERMEDIATE 2; Step A; To a solution of 5-trifluoromethyl-2-pyridinol (51.0 g, 307 mmol) and sodium acetate (26.2 g, 319 mmol) in glacial acetic acid (200 mL) was added bromine (16.7 mL, 325 mmol) and the resulting mixture was heated at 80 C. for 2.5 hours. The reaction was allow to cool to room temperature and then was evaporated under reduced pressure. The residue was neutralized with saturated NaHCO3 solution and extracted with ethyl acetate (3×200 mL). The organic layers were combined, dried over MgSO4, filtered, and evaporated in vacuo to yield 74.45 g (98.7%) of the crude product. 1H NMR (400 MHz, CDCl3) delta 8.04 (d, J=2.6 Hz, 1H), 7.89 (m, 1H).
98% With bromine; sodium acetate; In acetic acid; at 80℃; for 2.5h; To a solution of 5-trifluoromethyl-2-pyridinal (51 g, 310 mmol) and sodium acetate (26.2 g, 319 mmol) in glacial acetic acid (200 mL) was added bromine (16.7 mL, 325 mmol) and the resulting mixture was heated at 80 C. for 2.5 h. The reaction was allowed to cool to room temperature and then was evaporated under reduced pressure. The residue was neutralized with saturated NaHCO3 solution and extracted with ethyl acetate (3×200 mL). The organics were combined, dried over MgSO4, filtered, and evaporated in vacuo to yield 74.45 g (98%) of the crude product. 1H NMR (400 MHz, CDCl3) delta 8.04 (d, J=2.6 Hz, 1H), 7.89 (m, 1H).
98.7% With bromine; sodium acetate; In acetic acid; at 80℃; for 2.5h; To a solution of 5-trifluoromethyl-2-pyridinol (51.0 g, 307 mmol) and sodium acetate (26.2 g, 319 mmol) in glacial acetic acid (200 mL) was added bromine (16.7 mL, 325 mmol) and the resulting mixture was heated at 80 C. for 2.5 hours. The reaction was allow to cool to room temperature and then was evaporated under reduced pressure. The residue was neutralized with saturated NaHCO3 solution and extracted with ethyl acetate (3×200 mL). The organic layers were combined, dried over MgSO4, filtered, and evaporated in vacuo to yield 74.45 g (98.7%) of the crude product. 1H NMR (400 MHz, CDCl3) delta 8.04 (d, J=2.6 Hz, 1H), 7.89 (m, 1H).
95% With bromine; sodium acetate; In acetic acid; at 80℃; for 2h; To a solution of 5-TRIFLUOROMETHYL-2-PYRIDINOL (21.37 g, 131 mmol), and sodium acetate (11.23 g , 107 mmol) in glacial acetic acid was added bromine (6.94 ml, 135 mmol), and the resulting mixture stirred at 80 C for 2 hours. The cooled reaction mixture was evaporated and the residue basified by the addition of saturated NAHC03 (500 ml), and extracted with ethyl acetate (3 x 300 ml); the combined ethyl acetate layers were dried over MGS04, filtered and evaporated in vacuo to give the product (30.21 g, 95%) ; IH NMR 500MHZ (CDC13) 8 = 8.00 (1H, d, J = 2.29 Hz), 8.16 (LH, d, J=2. 29HZ).
85% With N-Bromosuccinimide; In N,N-dimethyl-formamide; for 2h; lambda/-bromosuccinimide (NBS, 39.0Og, 0.22 mol) is added portionwise to a solution of 5-(trifluoromethyl)pyridin-2-ol (30.0Og, 0.18 mol) in DMF (180 ml_), and the resulting mixture is stirred for 2 hours. The mixture is poured into water (1200 mL) and the precipitate was collected by filtration. The crystal is dried in vacuo to give the product as a white solid (1st crystal : 28.1Og). The filtrate is extracted with EtOAc, and the organic layer is concentrated.The residue is poured into water and the precipitate is collected by filtration. The crystal is dried in vacuo to give 3-bromo-5-(trifluoromethyl)pyridin-2-ol (2nd crystal : 9.65 g, total:37.75g, 85 % yield) as a yellow solid.1H-NMR (400MHz, CDCI3), delta (ppm): 7.86 (d, 1H), 8.02 (d, 1H), 13.17 (br, 1H).
With N-Bromosuccinimide; In N,N-dimethyl-formamide; for 2h; V-bromosuccinimide (NBS, 39.0Og, 0.22 mol) is added portionwise to a solution of 5- {trifluoromethyl)pyridin-2-ol (30.0Og, 0.18 mol) in DMF (180 ml_), and the resulting mixture is stirred for 2 hours. The mixture is poured into water (1200 ml.) and the precipitate is collected by filtration. The crystal is dried in vacuo to give the product as a white solid (1st crystal : 28.1Og). The filtrate is extracted with EtOAc, and the organic layer is concentrated. The residue is poured into water and the precipitate is collected by filtration. The crystal is dried in vacuo to give 3-bromo-5-(trifluoromethyl)pyridin-2-ol as a yellow solid. 1H-NMR (400MHz, CDCI3), delta (ppm): 7.86 (d, 1 H), 8.02 (d, 1 H), 13.17 (br, 1 H).
With N-Bromosuccinimide; In N,N-dimethyl-formamide; for 2h; lambda/-bromosuccinimide (NBS, 39.0Og, 0.22 mol) is added portionwise to a solution of 5- (trifluoromethyl)pyridin-2-ol (30.0Og, 0.18 mol) in DMF (180 mL), and the resulting mixture is stirred for 2 hours. The mixture is poured into water (1200 mL) and the precipitate is collected by filtration. The crystal is dried in vacuo to give the product as a white solid (1st crystal : 28.1Og). The filtrate is extracted with EtOAc, and the organic layer is concentrated. The residue is poured into water and the precipitate is collected by filtration. The crystal is dried in vacuo to give 3-bromo-5-(trifluoromethyl)pyridin-2-ol as a yellow solid. <n="45"/>Case 505091H-NMR (400MHz, CDCI3), delta (ppm): 7.86 (d, 1 H), 8.02 (d, 1H), 13.17 (br, 1 H).
With bromine; sodium acetate; In acetic acid; at 80℃; for 2.5h; INTERMEDIATE 4 To a solution of 5-trifluoromethyl-2-pyridinal (51 g, 310 mmol) and sodium acetate (26.2g, 319 mmol) in glacial acetic acid (200 mL) was added bromine (16.7 mL, 325 mmol) and the resulting mixture was heated at 80 C for 2.5 h. The reaction was allow to cool to room temperature and then was evaporated under reduced pressure. The residue was neutralized with saturated NaHC03 solution and extracted with ethyl acetate (3 x 200 mL). The organics were combined, dried over MgS04, filtered, and evaporated in vacuo to yield 74.45 g (98%) of the crude product.

  • 2
  • [ 76041-73-1 ]
  • [ 68-12-2 ]
  • [ 129904-48-9 ]
YieldReaction ConditionsOperation in experiment
100% <strong>[76041-73-1]3-Bromo-5-(trifluoromethyl)pyridin-2-ol</strong> (8.20 g, 31.2 mmol) was added in small portions to a suspension of sodium hydride (0.8575 g, 33.94 mmol) in anhydrous THF (76 mL) at room temperature. After complete addition, the reaction mixture was cooled to -78 C. and treated with a 1.7 M solution of tert-butyllithium in pentane (40.0 mL) which was added dropwise via a syringe over a period of 15 min. After stirring for 5 min, anhydrous DMF (8.16 mL, 105 mmol) was added slowly while maintaining the temperature below -50 C. The reaction mixture was then stirred overnight allowing it to warm to room temperature. The resulting light brown mixture was quenched by addition of a saturated NH4Cl solution. The pH of the solution was adjusted to 9-10 by addition of aqueous NaHCO3. The resulting solution was extracted with EtOAc four times. The combined extracts were dried (MgSO4), filtered and concentrated to provide a brown solid crude product (7.33 g, >100% crude yield). MS calculated for C7H4F3NO2 (M+H)+192; found 192.1.
74% With tert.-butyl lithium; sodium hydride; In tetrahydrofuran; at -78 - 20℃; for 10h; Under nitrogen, the substituted pyridine described in Step A (48.8g, 202 mmol) was added in small portions to a suspension OF NAH (8. 9 g, 220 mmol) in anhydrous tetrahydrofuran (500 mL). After complete addition of the intermediate, the reaction mixture was cooled to-78 C and treated with tert-butyllithium (260 ML, 444 mmol) added dropwise via syringe. After stirring for 5 min, N, N- dimethylformamide (50 ML, 707 mmol) was added slowly to maintain the temperature BELOW-50 C. The resulting mixture was then stirred for 10 h allowing it to warm to room temperature. The mixture was quenched with 2 N HC1 and then diluted with ethyl acetate (1000 mL). The organic layer was separated, washed with brine, dried over MGS04, and evaporated in vacuo. The desired product was precipitated out of ethyl acetate and hexanes and filtered to yield a light brown solid (28.55 g, 74%). 1H NMR (500 MHz, CD30D) 8 10.13 (s, 1H), 8.21 (s, 2H).
74% Step B; Under nitrogen, the substituted pyridine described in Step A, Intermediate 7 (48.8g, 202 mmol) was added in small portions to a suspension of NaH (8.9 g, 220 mmol) in anhydrous tetrahydrofuran (500 mL). After complete addition of the intermediate, the reaction mixture was cooled to-78 C and treated with tert-butyllithium (260 mL, 444 mmol) added dropwise via syringe. After stirring for 5 min, N, N- dimethylformamide (50 mL, 707 mmol) was added slowly to maintain the temperature below-50 C. The resulting mixture was then stirred for 10 h allowing it to warm to room temperature. The mixture was quenched with 2 N HCl and then diluted with ethyl acetate (1000 mL). The organic layer was separated, washed with brine, dried over MgS04, and evaporated in vacuo. The desired product was precipitated out of ethyl acetate and hexanes and filtered to yield a light brown solid (28.55 g, 74%). 1H NMR (500 MHz, CD30D) 8 10.13 (s, 1H), 8.21 (s, 2H).
74% Step B; Under nitrogen, the substituted pyridine described in Step A, Intermediate 8 (48.8g, 202 mmol) was added in small portions to a suspension of NaH (8. 9 g, 220 mmol) in anhydrous tetrahydrofuran (500 mL). After complete addition of the intermediate, the reaction mixture was cooled to-78 C and treated with tert-butyllithium (260 mL, 444 mmol) added dropwise via syringe. After stirring for 5 min, N, N-dimethylformamide (50 mL, 707 mmol) was added slowly to maintain the temperature below-50 C. The resulting mixture was then stirred for 10 h allowing it to warm to room temperature. The mixture was quenched with 2 N HC1 and then diluted with ethyl acetate (1000 mL). The organic layer was separated, washed with brine, dried over MgS04, and evaporated i71 vacuo. The desired product was precipitated out of ethyl acetate and hexanes and filtered to yield a light brown solid (28. 55 g, 74%).
73.8% Under nitrogen, the substituted pyridine, described in Step A (48.8 g, 202 mmol) was added by small portions to a suspension of NaH (8.9 g, 220 mmol) in anhydrous THF (500 mL). After complete addition of the intermediate, the reaction mixture was cooled to -78 C. and treated with tert-butyllithium (260 mL, 444 mmol) added dropwise via syringe. After stirring for 5 minutes, DMF (50 mL, 707 mmol) was added slowly to maintain the temperature below -50 C. The resulting mixture was then stirred for 10 hours allowing to warm to room temperature. The mixture was quenched with 2N HCl and then diluted with ethyl acetate (1000 mL). The organic layer was separated, washed with brine, dried over MgSO4, and evaporated in vacuo. The desired product was precipitated out of ethyl acetate and hexane and filtered to yield a light brown solid (28.55 g, 73.8%). 1H NMR (500 MHz, CD3OD) delta 10.13 (s, 1H), 8.21 (s, 2H).

  • 3
  • [ 76041-73-1 ]
  • [ 129904-48-9 ]
YieldReaction ConditionsOperation in experiment
74% Under nitrogen, the substituted pyridine described in Step A, Intermediate 11 (48.8 g, 202 mmol) was added in small portions to a suspension of NaH (8.9 g, 220 mmol) in anhydrous tetrahydrofuran (500 mL). After complete addition of the intermediate, the reaction mixture was cooled to -78 C. and treated with tert-butyllithium (260 mL, 444 mmol) added dropwise via syringe. After stirring for 5 min, N,N-dimethylformamide (50 mL, 707 mmol) was added slowly to maintain the temperature below -50 C. The resulting mixture was then stirred for 10 h allowing it to warm to room temperature. The mixture was quenched with 2 N HCl and then diluted with ethyl acetate (1000 mL). The organic layer was separated, washed with brine, dried over MgSO4, and evaporated in vacuo. The desired product was precipitated out of ethyl acetate and hexanes and filtered to yield a light brown solid (28.55 g, 74%). 1H NMR (500 MHz, CD3OD) delta 10.13 (s, 1H), 8.21 (s, 2H).
73.8% Under nitrogen, the substituted pyridine, described in Step A (48.8g, 202 mmol) was added by small portions to a suspension of NaH (8.9 g, 220 mmol) in anhydrous THF (500 ML). After complete addition of the intermediate, the reaction mixture was cooled to-78 C and treated with tert-butyllithium (260 mL, 444 mmol) added dropwise via syringe. After stirring for 5 minutes, DMF (50 mL, 707 mmol) was added slowly to maintain the temperature below- 50 C. The resulting mixture was then stirred for 10 hours allowing to warm to room temperature. The mixture was quenched with 2N HCI and then diluted with ethyl acetate (1000 mL). The organic layer was separated, washed with brine, dried over MGS04, and evaporated in vacuo. The desired product was precipitated out of ethyl acetate and hexane and filtered to yield a light brown solid (28.55 g, 73. 8%). H NMR (500 MHz, CD30D) 8 10.13 (s, 1H), 8.21 (s, 2H).
  • 4
  • [ 33252-63-0 ]
  • [ 76041-73-1 ]
YieldReaction ConditionsOperation in experiment
98% With bromine; sodium acetate; acetic acid; at 80℃; for 2.5h; INTERMEDIATE 7 Step A; To a solution of 5-trifluoromethyl-2-pyridinal (51 g, 310 mmol) and sodium acetate (26.2g, 319 mmol) in glacial acetic acid (200 mL) was added bromine (16.7 mL, 325 mmol) and the resulting mixture was heated at 80 C for 2.5 h. The reaction was allow to cool to room temperature and then was evaporated under reduced pressure. The residue was neutralized with saturated NaHC03 solution and extracted with ethyl acetate (3 x 200 mL). The organics were combined, dried over MgS04, filtered, and evaporated in vacuo to yield 74.45 g (98%) of the crude product. 1H NMR (400 MHz, CDC13) 8 8.04 (d, J=2.6 Hz, 1H), 7.89 (m, 1H).
98% With bromine; sodium acetate; acetic acid; at 80℃; for 2.5h; INTERMEDIATE 7; Step A; To a solution of 5-trifluoromethyl-2-pyridinal (51 g, 310 mmol) and sodium acetate (26.2g, 319 mmol) in glacial acetic acid (200 mL) was added bromine (16.7 mL, 325 mmol) and the resulting mixture was heated at 80 C for 2.5 h. The reaction was allow to cool to room temperature and then was evaporated under reduced pressure. The residue was neutralized with saturated NaHC03 solution and extracted with ethyl acetate (3 x 200 mL). The organics were combined, dried over MgS04, filtered, and evaporated ilz vacuo to yield 74.45 g (98%) of the crude product.
  • 5
  • [ 76041-73-1 ]
  • [ 71701-92-3 ]
YieldReaction ConditionsOperation in experiment
79% A mixture of <strong>[76041-73-1]3-bromo-5-(trifluoromethyl)pyridin-2-ol</strong> (37.75g, 0.16 mol) and phosphorus(lll) oxychloride (POCI3; 75 mL) is stirred at 1000C for 5 hours. After cooling to room temperature, the mixture is poured into ice-water, and extracted with CH2CI2 twice. The combined organic layer is washed with NaHCO3 aq., brine, dried over MgSO4, filtered and concentrated in vacuo. The crude mixture is purified by flash column chromatography to give 3-bromo-2-chloro-5-trifluoromethylpyridine (31.90 g, 79 % yield) as a white solid. 1H-NMR (400MHz, CDCI3), delta (ppm): 8.17 (m, 1H), 8.62 (d, 1 H).
A mixture of <strong>[76041-73-1]3-bromo-5-(trifluoromethyl)pyridin-2-ol</strong> (37.75g, 0.16 mol) and phosphorus(lll) oxychloride (POCI3; 75 mL) is stirred at 1000C for 5 hours. After cooling to room temperature, the mixture is poured into ice-water, and extracted with CH2CI2 twice. The combined organic layer is washed with NaHCO3 aq., brine, dried over MgSO4, filtered and concentrated in vacuo. The crude mixture is purified by flash column chromatography to give 3-bromo-2-chloro-5-trifluoromethylpyridine as a white solid. 1H-NMR (400MHz, CDCI3), delta (ppm): 8.17 (m, 1H), 8.62 (d, 1 H).
A mixture of <strong>[76041-73-1]3-bromo-5-(trifluoromethyl)pyridin-2-ol</strong> (37.75g, 0.16 mol) and phosphorus(lll) oxychloride (POCI3; 75 mL) is stirred at 1000C for 5 hours. After cooling to room temperature, the mixture is poured into ice-water, and extracted with CH2CI2 twice. The combined organic layer is washed with NaHCO3 aq., brine, dried over MgSO4, filtered and concentrated in vacuo. The crude mixture is purified by flash column chromatography to give 3-bromo-2-chloro-5-trifluoromethylpyridine as a white solid. 1H-NMR (400MHz, CDCI3), delta (ppm): 8.17 (m, 1 H), 8.62 (d, 1 H).
  • 6
  • [ 76041-73-1 ]
  • [ 439948-91-1 ]
  • C14H18BrF3N2O3 [ No CAS ]
  • 7
  • [ 76041-73-1 ]
  • N-(octaaminoquinoline)but-3-enamide [ No CAS ]
  • 4-(3-bromo-2-oxo-5-(trifluoromethyl)pyridin-1(2H)-yl)-N-(quinolin-8-yl)butanamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
50% With palladium diacetate; acetic acid; In acetonitrile; at 120℃; for 4h;Sealed tube; General procedure: Unless otherwise stated, the procedure was as follows. To a 1-dram (4 mL) vial equipped with a magnetic stir bar were added Pd(OAc)2 (4.4 mg, 0.02 mmol), alkene (0.2 mmol), acetic acid (6.0 mg, 0.1 mmol), nucleophile (0.3 mmol), and MeCN (0.1 mL). The vial was sealed with an unpunctured TFE septum-covered screw cap, and placed in a heating block that was pre-heated to 120 C. After the designated reaction time, the dark black reaction was purified either by flash column chromatography only or by flash column chromatography followed by an aqueous workup to produce the desired product.
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Chemical Structure| 33252-63-0

[ 33252-63-0 ]

5-(Trifluoromethyl)pyridin-2-ol

Similarity: 0.79

; ;