Sodium borohydride → 2-{2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-ethyl]-1H-pyrrolo[2,3-b]pyridin-5-yl}-ethanol

HRID 1515672Notes

Reaction equation

HRID 1515672 reaction equation
[CH:1]1([CH2:6][CH:7]([C:18]2[NH:29][C:21]3=[N:22][CH:23]=[C:24]([CH2:26][CH:27]=[O:28])[CH:25]=[C:20]3[CH:19]=2)[C:8]2[CH:13]=[CH:12][C:11]([S:14]([CH3:17])(=[O:16])=[O:15])=[CH:10][CH:9]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[BH4-].[Na+]>CO>[CH:1]1([CH2:6][CH:7]([C:18]2[NH:29][C:21]3=[N:22][CH:23]=[C:24]([CH2:26][CH2:27][OH:28])[CH:25]=[C:20]3[CH:19]=2)[C:8]2[CH:13]=[CH:12][C:11]([S:14]([CH3:17])(=[O:16])=[O:15])=[CH:10][CH:9]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86654504{2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-ethyl]-1H-pyrrolo[2,3-b]pyridin-5-yl}-acetaldehyde

Product 1

HCID 532509202-{2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-ethyl]-1H-pyrrolo[2,3-b]pyridin-5-yl}-ethanolYield 30.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of {2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-ethyl]-1H-pyrrolo[2,3-b]pyridin-5-yl}-acetaldehyde (65 mg, 0.158 mmol) in dry methanol at 0° C. (5 mL) was added sodium borohydride (60 mg, 1.58 mmol). The resulting mixture was stirred at room temperature for 2 h, quenched with a saturated aqueous ammonium chloride solution, extracted with ethyl acetate, washed with brine, and dried over anhydrous sodium sulfate. The solvent was evaporated in vacuo. Purification using a Waters automated flash system (column: Xterra 30 mm×100 mm, sample manager 2767, pump 2525, detector: ZQ mass and UV 2487, solvent system: acetonitrile and 0.1% ammonium hydroxide in water) afforded 2-{2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-ethyl]-1H-pyrrolo[2,3-b]pyridin-5-yl}-ethanol (20 mg, 30.7%) as a white solid: LC/MS m/e calcd for C23H28N2O3S [M+H]+ 413.56, observed 413.2; 1H NMR (400 MHz, CD3OD) δ ppm 7.99 (s, 1H), 7.87-7.92 (m, J=8.3 Hz, 2H), 7.79 (s, 1H), 7.58-7.63 (m, J=8.3 Hz, 2H), 6.36 (s, 1H), 4.31 (t, J=7.8 Hz, 1H), 3.78 (t, J=6.8 Hz, 2H), 3.10 (s, 3H), 2.90 (t, J=6.8 Hz, 2H), 2.25-2.33 (m, 1H), 2.07-2.15 (m, 1H), 1.62-1.87 (m, 5H), 1.46-1.56 (m, 2H), 1.19-1.31 (m, 2H).

Workup

  1. customquenched with a saturated aqueous ammonium chloride solution
  2. extractionextracted with ethyl acetate
  3. washwashed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated in vacuo
  6. customPurification

Sources & evidence

ORD record
ord-6786c9aaa8734930ad6fc735c7aec52a
Source dataset
uspto-grants-2012_07
Patent number
US08222416B2

Reaction notes

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