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

HRID 1515613Notes

Reaction equation

HRID 1515613 reaction equation
[CH:1]1([CH2:6][CH:7]([C:18]2[NH:28][C:21]3=[N:22][CH:23]=[C:24]([CH:26]=[O:27])[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:28][C:21]3=[N:22][CH:23]=[C:24]([CH2:26][OH:27])[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 86654499HCID 86654499, compound

Product 1

HCID 53250433{2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-ethyl]-1H-pyrrolo[2,3-b]pyridin-5-yl}-methanolYield 82%

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-carbaldehyde (104 mg, 0.26 mmol) in dry methanol (5 mL) was added sodium borohydride (40 mg, 1.05 mmol) at 0° C. The resulting mixture was stirred at room temperature for 2 h and then quenched with a saturated ammonium chloride solution, extracted with ethyl acetate and washed with brine, 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-cyclopentyl-1-(4-methanesulfonyl-phenyl)-ethyl]-1H-pyrrolo[2,3-b]pyridin-5-yl}-methanol (85 mg, 81%) as a white solid: LC/MS m/e calcd for C22H26N2O3S [M+H]+ 399.53, observed 399.1; 1H NMR (400 MHz, CDCl3) δ ppm 1.18 (m, 2H), 1.48 (m, 2H), 1.56-1.87 (m, 5H, H), 2.13 (m, 1H), 2.24 (m, 1H), 3.04 (s, 3H), 3.59 (br, 1H), 4.30 (t, J=7.7 Hz, 1H), 4.08 (s, 2H), 6.41 (s, 1H), 7.50 (d, J=8.2 Hz, 2H), 7.87 (d, J=8.2 Hz, 2H), 8.02 (s, 1H), 8.14 (br. s., 1H), 10.80 (br, 1H).

Workup

  1. customquenched with a saturated 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-5db0e1d456de4c759ebd1b9fbb29a540
Source dataset
uspto-grants-2012_07
Patent number
US08222416B2

Reaction notes

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