Sodium borohydride → HCID 44601272, compound

HRID 1177478Notes

Reaction equation

HRID 1177478 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[C:10]1[S:11][C:12]2[C:17]([N:18]=1)=[CH:16][CH:15]=[C:14]([C:19]1([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH2:21][CH2:20]1)[N:13]=2)[CH:5]=[O:6].[BH4-].[Na+]>C1COCC1.CO>[F:1][C:2]1[CH:3]=[C:4]([CH2:5][OH:6])[CH:7]=[CH:8][C:9]=1[C:10]1[S:11][C:12]2[C:17]([N:18]=1)=[CH:16][CH:15]=[C:14]([C:19]1([C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH2:20][CH2:21]1)[N:13]=2

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 591749073-Fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)benzaldehyde

Product 1

HCID 44601272HCID 44601272, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution at 0° C. of 3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine-2-yl)benzaldehyde (2.00 g, 5.34 mmol) in THF (50 mL) and MeOH (25 mL) was added sodium borohydride (0.188 mL, 5.34 mmol). The reaction mixture was allowed to warm up to ambient temperature. The crude reaction mixture, after 1 h, was concentrated in vacuo and purified by silica gel chromatography to afford (3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine-2-yl)phenyl)methanol. MS (ESI) m/z: calculated: 376.1: Observed: 377.0 (M++1).

Workup

  1. customThe crude reaction mixture
  2. concentrationwas concentrated in vacuo
  3. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-ce4a0e0a5c64401b8ba2ab7f817c0457
Source dataset
uspto-grants-2010_11
Patent number
US07842685B2

Reaction notes

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