Acetic Acid → 2-(4-isopropyl-phenyl)-7-methoxy-1-(2-methoxy-ethyl)-1H-benzoimidazole-5-carbaldehyde

HRID 1661916Notes

Reaction equation

[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:14]([CH2:15][CH2:16][O:17][CH3:18])[C:13]3[C:19]([O:25][CH3:26])=[CH:20][C:21]([C:23]#N)=[CH:22][C:12]=3[N:11]=2)=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[PH2]([O-])=[O:28].[Na+].C(O)(=O)C>[Ni].N1C=CC=CC=1>[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:14]([CH2:15][CH2:16][O:17][CH3:18])[C:13]3[C:19]([O:25][CH3:26])=[CH:20][C:21]([CH:23]=[O:28])=[CH:22][C:12]=3[N:11]=2)=[CH:6][CH:5]=1)([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 480 mg (1.37 mmol) 2-(4-isopropyl-phenyl)-7-methoxy-1-(2-methoxy-ethyl)-1H-benzoimidazole-5-carbonitrile (example 32), 15 mg Raney-Nickel (in water), 967 mg (11.0 mmol) sodium hypophosphite (in 10 ml water), 10 ml acetic acid and 20 ml pyridine is stirred for 6 h at 60° C. The catalyst is filtered off and the filtrate is poured on water and extracted (3×) with ethyl acetate. The combined organic layers are washed with water (2×) and brine, dried over MgSO4, filtered and concentrated in vacuo. The residue is purified by flash-chromatography on silica gel (hexane:EtOAc=1:1) to afford 330 mg of the title compound as a white crystalline solid.

Workup

filtrationThe catalyst is filtered off
additionthe filtrate is poured on water
extractionextracted (3×) with ethyl acetate
washThe combined organic layers are washed with water (2×) and brine
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated in vacuo
customThe residue is purified by flash-chromatography on silica gel (hexane:EtOAc=1:1)

Sources & evidence

ORD record: ord-e985b58174b94bf49a27b5778a6f549b
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08030497B2

Reaction notes

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