Sodium borohydride → {3-[2-(4-Chlorophenyl)imidazo[1,2-a]pyridin-6-yl]-2-fluorophenyl}methanol

HRID 1684908Notes

Reaction equation

HRID 1684908 reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:11]=[C:12]3[CH:17]=[CH:16][C:15]([C:18]4[C:19]([F:26])=[C:20]([CH:23]=[CH:24][CH:25]=4)[CH:21]=[O:22])=[CH:14][N:13]3[CH:27]=2)=[CH:6][CH:5]=1>CO>[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:11]=[C:12]3[CH:17]=[CH:16][C:15]([C:18]4[C:19]([F:26])=[C:20]([CH2:21][OH:22])[CH:23]=[CH:24][CH:25]=4)=[CH:14][N:13]3[CH:27]=2)=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86651935HCID 86651935, compound

Product 1

HCID 44231745{3-[2-(4-Chlorophenyl)imidazo[1,2-a]pyridin-6-yl]-2-fluorophenyl}methanolYield 57.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

162 mg of sodium borohydride are added portionwise to 150 mg of 3-[2-(4-chlorophenyl)imidazo[1,2-a]pyridin-6-yl]-2-fluorobenzaldehyde dissolved in 20 ml of methanol. The mixture is subsequently stirred at ambient temperature for 2 hours and then the solvent is evaporated under reduced pressure. The residue is taken up between water and dichloromethane and the organic phase is separated, dried over sodium sulphate and evaporated under reduced pressure. The residue is purified by chromatography on silica gel, elution being carried out with a dichloromethane/methanol 98/02 mixture. 87 mg of compound are obtained.

Workup

  1. customthe solvent is evaporated under reduced pressure
  2. customthe organic phase is separated
  3. dry with materialdried over sodium sulphate
  4. customevaporated under reduced pressure
  5. customThe residue is purified by chromatography on silica gel, elution

Sources & evidence

ORD record
ord-6f275abcd02440a383bcc838b6fa7230
Source dataset
uspto-grants-2012_04
Patent number
US08148370B2

Reaction notes

Loading…