Sodium borohydride → HCID 53237073, compound

HRID 1897617Notes

Reaction equation

HRID 1897617 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[C:8]([C:10]3[CH:11]=[N:12][CH:13]=[CH:14][C:15]=3[CH:16]=[O:17])[N:7]([CH3:18])[C:6]=2[CH:19]=1.[BH4-].[Na+]>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[C:8]([C:10]3[CH:11]=[N:12][CH:13]=[CH:14][C:15]=3[CH2:16][OH:17])[N:7]([CH3:18])[C:6]=2[CH:19]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86674841HCID 86674841, compound

Product 1

HCID 53237073HCID 53237073, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3-(6-chloro-1-methyl-1H-benzoimidazol-2-yl)-pyridine-4-carbaldehyde (50 mg, 0.184 mmol) in MeOH (4 mL) at 0° C. was added sodium borohydride (10.44 mg, 0.276 mmol). The mixture was stirred at room temperature for 30 min. The reaction was quenched with water (0.5 mL) and the mixture was concentrated in vacuo. The crude was taken up in MeOH (5 mL) and purified on HPLC using RP18 column and gradient 0.1% aqueous NH4OH in acetonitrile to afford pure product [3-(6-chloro-1-methyl-1H-benzoimidazol-2-yl)-pyridin-4-yl]-methanol as a white color solid. 1H NMR (400 MHz, MeOD) δ ppm 3.76 (s, 3H), 4.64 (s, 2H), 7.38 (dd, J=8.7, 1.9 Hz, 1H), 7.71 (d, J=8.6 Hz, 1H), 7.73 (d, J=2.0 Hz, 1H), 7.84 (d, J=5.1 Hz, 1H), 8.69 (s, 1H), 8.79 (d, J=5.3 Hz, 1H); HRMS: (ESI) m/z 274.0739 [(M+H)+ Calcd for C14H12ClN3O 274.0747].

Workup

  1. customThe reaction was quenched with water (0.5 mL)
  2. concentrationthe mixture was concentrated in vacuo
  3. custompurified on HPLC

Sources & evidence

ORD record
ord-04b8f452e2ae485bb275b22a83c38785
Source dataset
uspto-grants-2013_08
Patent number
US08519134B2

Reaction notes

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