Sodium borohydride → [5-(2-Chloro-pyridin-4-ylethynyl)-3-(4-fluoro-phenyl)-2-methyl-3H-imidazol-4-yl]-methanol

HRID 2067943Notes

Reaction equation

HRID 2067943 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]#[C:9][C:10]2[N:14]=[C:13]([CH3:15])[N:12]([C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)[C:11]=2[CH:23]=[O:24])[CH:5]=[CH:4][N:3]=1.[BH4-].[Na+]>CO>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]#[C:9][C:10]2[N:14]=[C:13]([CH3:15])[N:12]([C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)[C:11]=2[CH2:23][OH:24])[CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 866029665-(2-Chloro-pyridin-4-ylethynyl)-3-(4-fluoro-phenyl)-2-methyl-3H-imidazole-4-carbaldehyde

Product 1

HCID 11530240[5-(2-Chloro-pyridin-4-ylethynyl)-3-(4-fluoro-phenyl)-2-methyl-3H-imidazol-4-yl]-methanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 100 mg (0.29 mmol) 5-(2-Chloro-pyridin-4-ylethynyl)-3-(4-fluoro-phenyl)-2-methyl-3H-imidazole-4-carbaldehyde (example 26) in 5 ml of methanol were added at 0° C. 11 mg (0.29 mmol) of sodium borohydride, and the mixture was stirred for 1 h at 0° C. The reaction mixture was quenched with sat. NaHCO3− solution and evaporated. The residue was extracted with water and ethyl acetate. The combined organic extracts were dried with sodium sulfate, filtered and evaporated. The crude product was purified by flash chromatography on silica gel (heptane/ethyl acetate 1:1). The desired compound was obtained as a white solid (40 mg, 40%), MS: m/e=342.1 (M+H+).

Workup

  1. customThe reaction mixture was quenched with sat. NaHCO3− solution
  2. customevaporated
  3. extractionThe residue was extracted with water and ethyl acetate
  4. dry with materialThe combined organic extracts were dried with sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude product was purified by flash chromatography on silica gel (heptane/ethyl acetate 1:1)

Sources & evidence

ORD record
ord-c6e7e0c8823344a38b139e628c0f4d96
Source dataset
uspto-grants-2012_10
Patent number
US08293916B2

Reaction notes

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