Sodium borohydride → Racemic 1-{3-[2-(4-chlorophenyl)imidazo[1,2-a]pyridin-6-yl]phenyl}ethanol

HRID 606016Notes

Reaction equation

HRID 606016 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[CH:19]=[C:20]([C:24](=[O:26])[CH3:25])[CH:21]=[CH:22][CH:23]=4)=[CH:14][N:13]3[CH:27]=2)=[CH:6][CH:5]=1>CO>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[N:11]=[C:12]3[CH:17]=[CH:16][C:15]([C:18]4[CH:19]=[C:20]([CH:24]([OH:26])[CH3:25])[CH:21]=[CH:22][CH:23]=4)=[CH:14][N:13]3[CH:27]=2)=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 670470901-{3-[2-(4-Chlorophenyl)imidazo[1,2-a]pyridin-6-yl]phenyl}ethanone

Product 1

HCID 67046247Racemic 1-{3-[2-(4-chlorophenyl)imidazo[1,2-a]pyridin-6-yl]phenyl}ethanolYield 82.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

164 mg of sodium borohydride are added portionwise to 150 mg of 1-{3-[2-(4-chloro-phenyl)imidazo[1,2-a]pyridin-6-yl]phenyl}ethanone (compound obtained in 8.1) dissolved in 20 ml of methanol. The mixture is then stirred at ambient temperature for one hour and the solvent is then evaporated off under reduced pressure. The residue is taken up in between water and dichloromethane, the organic phase is separated by settling out and dried over sodium sulphate and the solvent is then evaporated off under reduced pressure. The residue is triturated in diisopropyl ether and recovered by filtration and then dried in a dessicator under reduced pressure. 124 mg of compound are obtained. Mp=174-176° C. 1H NMR (DMSO-d6, δ in ppm): 1.37 (d, J=6.5 Hz, 3H); 4.79 (m, 1H); 5.19 (d, J=4.2 Hz, 1H); from 7.31 to 7.69 (m, 8H); 7.97 (m, J=8.6 Hz, 2H); 8.41 (s, 1H); 8.84 (m, 1H). M+H=349.

Workup

  1. customthe solvent is then evaporated off under reduced pressure
  2. customthe organic phase is separated
  3. dry with materialdried over sodium sulphate
  4. customthe solvent is then evaporated off under reduced pressure
  5. customThe residue is triturated in diisopropyl ether
  6. filtrationrecovered by filtration
  7. customdried in a dessicator under reduced pressure

Sources & evidence

ORD record
ord-a91f2fc101f94a0394675b1b50071a80
Source dataset
uspto-grants-2011_03
Patent number
US07915284B2

Reaction notes

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