Hydrogen Peroxide → 2-(6-chloro-4-(4-fluoro-1H-indol-2-yl)pyridin-3-yl)propan-1-ol

HRID 595720Notes

Reaction equation

HRID 595720 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]2[NH:9][C:10]3[C:15]([CH:16]=2)=[C:14]([F:17])[CH:13]=[CH:12][CH:11]=3)[C:5]([C:18]([CH3:20])=[CH2:19])=[CH:4][N:3]=1.[OH:21]O>O>[Cl:1][C:2]1[N:3]=[CH:4][C:5]([CH:18]([CH3:20])[CH2:19][OH:21])=[C:6]([C:8]2[NH:9][C:10]3[C:15]([CH:16]=2)=[C:14]([F:17])[CH:13]=[CH:12][CH:11]=3)[CH:7]=1

Participants

4

Reactant 2

HCID 784Hydrogen PeroxideHCID 903338462-(2-chloro-5-(prop-1-en-2-yl)pyridin-4-yl)-4-fluoro-1H-indole

Product 1

HCID 903334522-(6-chloro-4-(4-fluoro-1H-indol-2-yl)pyridin-3-yl)propan-1-olYield 36%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a degassed solution of 2-(2-chloro-5-(prop-1-en-2-yl)pyridin-4-yl)-4-fluoro-1H-indole (50 mg, 0.17 mmol) was added BH3-DMS (0.5 mL) under N2 protection at 0° C., and the mixture was stirred for 1 hour. Then NaBO3.4H2O (60 mg, 0.34 mmol) and H2O2 (0.2 mL) was added under N2 protection at 0° C. for 0.5 hours, and the reaction mixture was stirred at RT for 2 hours. After diluted with H2O and extracted with EtOAc, the combined organic layer was washed with H2O, brine, dried over Na2SO4, and the residue was purified by prep-HPLC to give 2-(6-chloro-4-(4-fluoro-1H-indol-2-yl)pyridin-3-yl)propan-1-ol (20 mg, yield: 36%). 1H-NMR (CDCl3, 400 MHz) δ 10.86 (s, 1H), 8.17 (s, 1H), 7.33 (s, 1H), 7.18 (s, 1H), 7.06˜7.10 (m, 1H), 6.71˜7.76 (m, 2H), 4.10 (s, 1H), 3.95 (s, 1H), 3.75 (t, J=12.0 Hz 1H), 3.42˜3.51 (m, 1H), 1.14 (d, J=8.0 Hz, 3H). MS (M+H)+: 305/307.

Workup

  1. stirringthe reaction mixture was stirred at RT for 2 hours
  2. extractionextracted with EtOAc
  3. washthe combined organic layer was washed with H2O, brine
  4. dry with materialdried over Na2SO4
  5. customthe residue was purified by prep-HPLC

Sources & evidence

ORD record
ord-3975f611c4ab461481cf59cc49a80e09
Source dataset
uspto-grants-2016_01
Patent number
US09243002B2

Reaction notes

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