Sodium borohydride → HCID 69063770, compound

HRID 1868338Notes

Reaction equation

HRID 1868338 reaction equation
[CH3:1][N:2]1[N:6]=[C:5]2[CH:7]=[CH:8][C:9]([C:11]3[N:12]=[C:13]([CH:23]=[O:24])[NH:14][C:15]=3[C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([CH3:22])[N:17]=3)=[CH:10][C:4]2=[N:3]1.[BH4-].[Na+]>CO>[CH3:1][N:2]1[N:6]=[C:5]2[CH:7]=[CH:8][C:9]([C:11]3[N:12]=[C:13]([CH2:23][OH:24])[NH:14][C:15]=3[C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([CH3:22])[N:17]=3)=[CH:10][C:4]2=[N:3]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86592586HCID 86592586, compound

Product 1

HCID 69063770HCID 69063770, compoundYield 64.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-(2-methyl-2H-benzotriazol-5-yl)-5-(6-methyl-pyridin-2-yl)-1H-imidazole-2-carbaldehyde (20 mg, 0.063 mmol) was dissolved in 2 ml anhydrous methanol. Sodium borohydride (3 mg, 0.069 mmol) was added and the reaction stirred at room temperature for 1 hour. The reaction was quenched with water and solvent was removed by rotary evaporation. The residue was purified on Biotage Flash 12S silica gel column using chloroform/methanol gradient system (97:3 to 95:5, respectively) as eluent to afford [4-(2-methyl-2H-benzotriazol-5-yl)-5-(6-methyl-pyridin-2-yl)-1H-imidazol-2-yl]-methanol (13 mg, 64% yield) as a white solid. HPLC tR=3.18 min, LC-MS=321 (M+1).

Workup

  1. customThe reaction was quenched with water and solvent
  2. customwas removed by rotary evaporation
  3. customThe residue was purified on Biotage Flash 12S silica gel column

Sources & evidence

ORD record
ord-8f6b859f079f4e21ae438f8d08ec4e8c
Source dataset
uspto-grants-2009_12
Patent number
US07635702B2

Reaction notes

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