Sodium borohydride → HCID 57537679, compound

HRID 1693736Notes

Reaction equation

HRID 1693736 reaction equation
[Cl:1][C:2]1[C:7]([C:8]2[CH:9]=[C:10]([C:14]([C:16]3[O:17][CH:18]=[CH:19][N:20]=3)=[O:15])[CH:11]=[CH:12][CH:13]=2)=[CH:6][N:5]=[C:4]2[N:21]([CH2:31][O:32][CH2:33][CH2:34][Si:35]([CH3:38])([CH3:37])[CH3:36])[CH:22]=[C:23]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[F:30])[C:3]=12.[BH4-].[Na+]>CO>[Cl:1][C:2]1[C:7]([C:8]2[CH:9]=[C:10]([CH:14]([C:16]3[O:17][CH:18]=[CH:19][N:20]=3)[OH:15])[CH:11]=[CH:12][CH:13]=2)=[CH:6][N:5]=[C:4]2[N:21]([CH2:31][O:32][CH2:33][CH2:34][Si:35]([CH3:38])([CH3:37])[CH3:36])[CH:22]=[C:23]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[F:30])[C:3]=12

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 57537624HCID 57537624, compound

Product 1

HCID 57537679HCID 57537679, compoundYield 72.82%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of {3-[4-chloro-3-(2-fluoro-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-phenyl}-oxazol-2-yl-methanone (22 mg, 0.040 mmol) in MeOH (0.25 mL) was added to a cold suspension (0° C.) of NaBH4 (1.59 mg, 0.042 mmol) in MeOH (0.25 mL). After 1 h, the mixture was quenched by addition of saturated ammonium chloride and the solution was concentrated to a solid. The residue was triturated with ethyl acetate to afford {3-[4-chloro-3-(2-fluoro-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-phenyl}-oxazol-2-yl-methanol (16 mg, 72.82%). MS: m/z 550 (M+H+).

Workup

  1. customthe mixture was quenched by addition of saturated ammonium chloride
  2. concentrationthe solution was concentrated to a solid
  3. customThe residue was triturated with ethyl acetate

Sources & evidence

ORD record
ord-27d0f130bbf743bda156ba6fea3ff744
Source dataset
uspto-grants-2012_04
Patent number
US08158647B2

Reaction notes

Loading…