Sodium borohydride → HCID 24771669, compound

HRID 645369Notes

Reaction equation

HRID 645369 reaction equation
[BH4-].[Na+].[C:3]([C:11]1[CH:12]=[CH:13][C:14]2[N:15]([CH:17]=[C:18]([C:20]([NH:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[O:21])[N:19]=2)[CH:16]=1)(=[O:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>CO>[OH:10][CH:3]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[C:11]1[CH:12]=[CH:13][C:14]2[N:15]([CH:17]=[C:18]([C:20]([NH:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[O:21])[N:19]=2)[CH:16]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydride2×HCID 68615384HCID 68615384, compound

Product 1

HCID 24771669HCID 24771669, compoundYield 77.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

17.4 mg of sodium borohydride are added to a suspension, cooled to 0° C., of 157 mg of 6-benzoyl-N-phenylimidazo[1,2-a]pyridine-2-carboxamide in 10 ml of methanol. The reaction mixture is stirred for 16 hours, while allowing the temperature to rise to 20° C. 20 mg of sodium borohydride are added and the mixture is stirred at 20° C. for a further 1.5 hours. After evaporating to dryness, the residue is taken up in 50 ml of water and 200 ml of ethyl acetate. The organic phase is separated by settling, dried and concentrated to dryness under reduced pressure to give 122 mg of 6-[hydroxy(phenyl)methyl]-N-phenylimidazo[1,2-a]pyridine-2-carboxamide in the form of a white solid.

Workup

  1. customto rise to 20° C
  2. stirringthe mixture is stirred at 20° C. for a further 1.5 hours
  3. customAfter evaporating to dryness
  4. customThe organic phase is separated
  5. customdried
  6. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-acb39054d57943dcb9a27cb55f99cce4
Source dataset
uspto-grants-2010_04
Patent number
US07704989B2

Reaction notes

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