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[ CAS No. 858629-06-8 ] {[proInfo.proName]}

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Chemical Structure| 858629-06-8
Chemical Structure| 858629-06-8
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Product Details of [ 858629-06-8 ]

CAS No. :858629-06-8 MDL No. :MFCD06739145
Formula : C7H4FIN2 Boiling Point : No data available
Linear Structure Formula :- InChI Key :CZUPBTJBMHZBTJ-UHFFFAOYSA-N
M.W : 262.02 Pubchem ID :24728241
Synonyms :

Calculated chemistry of [ 858629-06-8 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 48.77
TPSA : 28.68 ?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) : -6.24 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.38
Log Po/w (XLOGP3) : 2.34
Log Po/w (WLOGP) : 2.73
Log Po/w (MLOGP) : 2.73
Log Po/w (SILICOS-IT) : 3.42
Consensus Log Po/w : 2.52

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.54
Solubility : 0.0748 mg/ml ; 0.000286 mol/l
Class : Soluble
Log S (Ali) : -2.58
Solubility : 0.687 mg/ml ; 0.00262 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.14
Solubility : 0.0189 mg/ml ; 0.0000719 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 2.16

Safety of [ 858629-06-8 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P305+P351+P338 UN#:
Hazard Statements:H302-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 858629-06-8 ]

* 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 [ 858629-06-8 ]

[ 858629-06-8 ] Synthesis Path-Downstream   1~13

  • 1
  • [ 24424-99-5 ]
  • [ 858629-06-8 ]
  • [ 944904-49-8 ]
YieldReaction ConditionsOperation in experiment
With dmap; triethylamine; at 20℃; General procedure: 3-Iodo-1H-indazole (S1, 5.00 g, 19.5 mmol) was placed in a round-bottom flask and dissolved in tetrahydrofuran (100 mL). 4-Dimethylaminopyridine (0.24 g, 1.9 mmol, 0.1 equiv) was then added, followed by di-tert-butyl dicarbonate (5.4 mL, 24 mmol, 1.2 equiv). Triethylamine (5.4 mL, 39 mmol, 2.0 equiv) was slowly added to the clear, brown solution by syringe. The resulting solution was stirred at room temperature until it was complete as determined by TLC. The reaction was then diluted with water (75 mL) and ethyl acetate (50 mL). After separating the layers, the aqueous phase was extracted with additional ethyl acetate (3 × 50 mL). The combined organic layers were washed with brine (100 mL), then shaken over magnesium sulfate, filtered, and concentrated under reduced pressure to give the crude product. This material was purified by column chromatography over silica gel (hexanes/ethyl acetate: 100/0 to 90/10) to give the title compound as an orange solid (6.20 g, 93%).
  • 2
  • [ 348-26-5 ]
  • [ 858629-06-8 ]
YieldReaction ConditionsOperation in experiment
96.1% With iodine; potassium hydroxide; In N,N-dimethyl-formamide; at 20℃; for 0.5h; To a solution of 5-fluoro-1H-indazole (2.0 g, 14.0 mmol) in DIVIF (50 mL) was added ‘2 (7.46 g, 28.0 mmol) and KOH (2.4 g, 42 mmol), the mixture was stirred at room temperature for 0.5 hr. The reaction was monitored by TLC. After completion, the mixture was filtered, the filtrate was concentrated in vacuum to give a residue, which was purified by a silica gel column (PE/EA = 3/1) to afford 5-fluoro-3-iodo-1H-indazole (3.7 g, yield: 96.1%) as a white solid. ‘H NIVIR (400 IVIHz, DMSO-d6): ? = 13.64 (s, 1H), 7.63 (dd, J= 4.8, 4.4 Hz, 1H), 7.38-7.30 (m, 1H), 7.20 (dd, J=6.4,2.4Hz, 1H).
95.1% With iodine; potassium hydroxide; In N,N-dimethyl-formamide; at 20℃; for 1h; 5-Fluoro-1H-indazole (10.00 g, 73.46 mmol) was added into N,N-dimethylformamide(80 mL), then Iodine (28.0 g, 110 mmol) and potassium hydroxide (6.20 g, 110 mmol) wereadded. After addition, the mixture was reacted for 1 hour at room temperature. The reactionmixture was poured into aqueous sodium thiosulfate solution (300 mL, 5%). The resultingmixture was extracted with ethyl acetate (100 mL x 2). The combined organic layers werewashed with water (100 mL) and saturated brine (100 mL), dried over anhydrous sodium sulfate,and filtered. The filtrate was concentrated on a rotary evaporator to give a light yellow solid(18.3 g, 95.1 %)
87% With iodine; potassium hydroxide; In N,N-dimethyl-formamide; at 20℃; for 3h; General procedure: 3-Iodoindazoles were obtained by direct iodination of commercial indazoles by the method previously described by Bocchi [28] with slight modifications. A solution of 1H-indazole (3 g, 25.4 mmol), iodine (12.7 g, 50.03 mmol) and potassium hydroxide (5.34 g, 95.25 mmol)in DMF (7 mL) was stirred for 3 h at room temperature. The reaction was quenched by dilution with saturated solution of sodium bisulfite (150 mL) and a precipitated was formed. The precipitated was filtered over vacuum and washed with water (3 × 30 mL). The solid was left to dry at 30 C in a vacuum oven overnight obtaining 6.17 g of a pale yellow solid. Yield: 100%; m.p.: 136-138 C (lit.:[36] 134-136 C); IR (KBr) ν (cm-1): 3086 (NH); 424 (C-I). 1H-NMR δ (ppm): 13.50 (1H, s, H-1); 7.55(1H, d, J = 8.6 Hz, H-7); 7.45-7.40 (2H, m, H-6 and H-4); 7.19 (1H, dd, J = 7.5 Hz, H-5). 13C-NMR δ(ppm): 140.41; 127.22; 126.79; 121.23; 120.39; 110.51; 93.49; HRMS calculated for C7H5IN2: 243.9497,Found: 243.9499.3-Iodo-1H-indazole (1a). 3-Iodoindazoles were obtained by direct iodination of commercial indazoles by the method previously described by Bocchi [28] with slight modifications. A solution of 1H-indazole(3 g, 25.4 mmol), iodine (12.7 g, 50.03 mmol) and potassium hydroxide (5.34 g, 95.25 mmol) in DMF(7 mL) was stirred for 3 h at room temperature. The reaction was quenched by dilution with saturated solution of sodium bisulfite (150 mL) and a precipitated was formed. The precipitated was filtered over vacuum and washed with water (3 30 mL). The solid was left to dry at 30 C in a vacuum oven overnight obtaining 6.17 g of a pale yellow solid. Yield: 100%; m.p.: 136-138 C (lit.: [36] 134-136 C)
  • 3
  • [ 67-56-1 ]
  • [ 201230-82-2 ]
  • [ 858629-06-8 ]
  • [ 78155-73-4 ]
  • 4
  • [ 110-68-9 ]
  • [ 201230-82-2 ]
  • [ 858629-06-8 ]
  • [ 1352415-07-6 ]
YieldReaction ConditionsOperation in experiment
With iodine; sodium hydroxide; In methanol; at 20℃; for 48h; General procedure: 3-lodo-1H-indazole Iodine (5.8 g, 22.9 mmol) was added in portions over approximately 20 min to a solution of indazole (2.5 g, 21.7 mmol) in methanol (63 ml) and 2N sodium hydroxide solution (65 ml). The mixture remained colourless and a white precipitate slowly formed. The mixture was stirred at room temperature 48 h. The mixture was cooled in an ice-bath and 7.5 ml of concentrated hydrochloric acid was slowly added. The mixture was further acidified with 2N hydrochloric acid. 20% w/v Sodium thiosulfate pentahydrate solution was added until the iodine colour disappeared. The precipitate was filtered, washed with water and dried in the oven at 50 oC to constant weight. The solid was taken up in methanol, filtered and the filtrated was evaporated under reduced pressure to give 5.0 g (20.6 mmol, 95%) of the title compound as a white solid. Purity 100%.1H NMR (300 MHz, CHLOROFORM-d) δ ppm 7.43-7.59 (m, 3H), 7.21-7.26 (m, 1H).UPLC/MS (3 min) retention time 1.56 min.LRMS: m/z 245 (M+1).
With iodine; sodium hydroxide; In methanol; at 20℃; for 48h; General procedure: Iodine (5.8 g, 22.9 mmol) was added in portions over approximately 20 min to a solution of indazole (2.5 g, 21 .7 mmol) in methanol (63 ml) and 2N sodium hydroxide solution (65 ml). The mixture remained colourless and a white precipitate slowly formed. The mixture was stirred at room temperature 48 h. The mixture was cooled in an ice-bath and 7.5 ml of concentrated hydrochloric acid was slowly added. The mixture was further acidified with 2N hydrochloric acid. 20% w/v Sodium thiosulfate pentahydrate solution was added until the iodine colour disappeared. The precipitate was filtered, washed with water and dried in the oven at 50 C to constant weight. The solid was taken up in methanol, filtered and the filtrated was evaporated under reduced pressure to give 5.0 g (20.6 mmol, 95%) of the title compound as a white solid. Purity 100%. 1 H NMR (300 MHz, CHLOROFORM-d) δ ppm 7.43-7.59 (m, 3H), 7.21 -7.26 (m, 1 H). UPLC/MS (3 min) retention time 1 .56 min. LRMS: m/z 245 (M+1 ).
  • 6
  • [ 858629-06-8 ]
  • C16H13FN2O2 [ No CAS ]
  • 7
  • [ 858629-06-8 ]
  • [ 57614-63-8 ]
  • 8
  • [ 353-83-3 ]
  • [ 858629-06-8 ]
  • [ 1613515-95-9 ]
YieldReaction ConditionsOperation in experiment
46% With potassium carbonate; In acetonitrile;Reflux; General procedure: Potassium carbonate (791 mg, 5.7 mmol) was added to a solution of 3-iodoindazole (700 mg, 2.9 mmol) and 2-chloroethyl methyl ether (406 mg, 4.3 mmol) in ACN (20 mL) at rt. The reaction was heated to reflux overnight, and then was filtered and concentrated. The residue was purified by silica gel chromatography (15%-50% EtOAc/hexanes) to give 530 mg (63%) of the title compound as a light yellow oil. The title compound was prepared in 46% yield from 5-fluoro-3-iodo-indazole and 1,1,1-trifluoro-2-iodoethane according to the general procedure for Preparation 10A. The minor isomer was not isolated or characterized. 1H NMR (400 MHz, CDCl3): δ 4.91-4.97 (2H, m), 7.17 (1H, dd, J=2.0, 8.0 Hz), 7.30 (1H, td, J=2.0, 8.4 Hz), 7.38 (1H, dd, J=3.6, 9.2 Hz).
  • 9
  • [ 858629-06-8 ]
  • [ 100-39-0 ]
  • [ 1613515-96-0 ]
YieldReaction ConditionsOperation in experiment
75% With potassium carbonate; In acetonitrile;Reflux; General procedure: Potassium carbonate (791 mg, 5.7 mmol) was added to a solution of 3-iodoindazole (700 mg, 2.9 mmol) and 2-chloroethyl methyl ether (406 mg, 4.3 mmol) in ACN (20 mL) at rt. The reaction was heated to reflux overnight, and then was filtered and concentrated. The residue was purified by silica gel chromatography (15%-50% EtOAc/hexanes) to give 530 mg (63%) of the title compound as a light yellow oil. The title compound was prepared in 75% yield from 5-fluoro-3-iodo-indazole and benzyl bromide according to the general procedure for Preparation 10A. The minor isomer was not isolated or characterized. 1H NMR (400 MHz, CDCl3): δ 5.59 (2H, s), 7.11-7.21 (5H, m), 7.23-7.31 (3H, m).
  • 10
  • [ 3814-30-0 ]
  • [ 858629-06-8 ]
  • [ 1613516-08-7 ]
  • [ 1613516-09-8 ]
YieldReaction ConditionsOperation in experiment
72%; 18% With potassium carbonate; In acetonitrile;Reflux; General procedure: Potassium carbonate (791 mg, 5.7 mmol) was added to a solution of 3-iodoindazole (700 mg, 2.9 mmol) and 2-chloroethyl methyl ether (406 mg, 4.3 mmol) in ACN (20 mL) at rt. The reaction was heated to reflux overnight, and then was filtered and concentrated. The residue was purified by silica gel chromatography (15%-50% EtOAc/hexanes) to give 530 mg (63%) of the title compound as a light yellow oil. The title compounds were prepared from 5-fluoro-3-iodo-indazole and (bromomethyl)cyclopentane according to the procedure for Preparation 10A. [0365] 1-(cyclopentylmethyl)-<strong>[858629-06-8]5-fluoro-3-iodo-1H-indazole</strong> (72%) was isolated as the major isomer eluting first. 1H NMR (400 MHz, CDCl3): δ 1.25-1.32 (2H, m), 1.50-1.65 (6H, m), 2.48-2.56 (1H, m), 4.27 (2H, d, J=7.5 Hz), 7.09 (1H, dd, J=8.3, 2.3 Hz), 7.18 (1H, td, J=8.9, 2.4 Hz), 7.32 (1H, dd, J=9.1, 4.0 Hz). [M+H] calc'd for C13H14FIN2, 345. found 345. [0366] 2-(cyclopentylmethyl)-5-fluoro-3-iodo-2H-indazole (18%) was isolated as the minor isomer eluting second. 1H NMR (400 MHz, CDCl3): δ 1.33-1.42 (2H, m), 1.56-1.73 (6H, m), 2.62-2.70 (1H, m), 4.41 (2H, d, J=7.6 Hz), 7.00 (1H, dd, J=8.8, 2.4 Hz), 7.09 (1H, td, J=9.2, 2.4 Hz), 7.65 (1H, dd, J=9.3, 4.5 Hz). [M+H] calc'd for C13H14FIN2, 345. found 345.
  • 11
  • [ 858629-06-8 ]
  • [ 107-06-2 ]
  • [ 1613516-88-3 ]
YieldReaction ConditionsOperation in experiment
67% With potassium carbonate; In acetonitrile;Reflux; To a solution of 5-fluoro-3-iodo-indazole (3.0 g, 11.5 mmol) and 1,2-dichloroethane (5.7 g, 57.3 mmol) in ACN (50 mL) was added K2CO3 (3.2 g, 22.9 mmol) at rt. The reaction was stirred overnight at reflux. The reaction mixture was filtered and concentrated in vacuo. Purification by silica gel chromatography (30:1:5 hexanes/EtOAc/DCM) gave 2.5 g (67%) of the title compound as a yellow solid. 1H NMR (300 MHz, CDCl3): δ 3.97 (2H, t, J=6.0 Hz), 4.69 (2H, t, J=6.0 Hz), 7.13 (1H, dd, J=1.8, 7.8 Hz), 7.22-7.29 (1H, m), 7.42 (1H, dd, J=3.9, 9.3 Hz).
  • 12
  • [ 858629-06-8 ]
  • [ 1613515-93-7 ]
  • 13
  • [ 858629-06-8 ]
  • [ 1613516-39-4 ]
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