Dimethylformamide → 2-(4-Isopropyl-phenyl)-7-methoxy-1-(2-methoxy-ethyl)-1H-benzoimidazole-5-carbonitrile

HRID 1661909Notes

Reaction equation

Br[C:2]1[CH:23]=[C:22]([O:24][CH3:25])[C:5]2[N:6]([CH2:18][CH2:19][O:20][CH3:21])[C:7]([C:9]3[CH:14]=[CH:13][C:12]([CH:15]([CH3:17])[CH3:16])=[CH:11][CH:10]=3)=[N:8][C:4]=2[CH:3]=1.[CH3:26][N:27](C=O)C>[C-]#N.[Zn+2].[C-]#N.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH:15]([C:12]1[CH:11]=[CH:10][C:9]([C:7]2[N:6]([CH2:18][CH2:19][O:20][CH3:21])[C:5]3[C:22]([O:24][CH3:25])=[CH:23][C:2]([C:26]#[N:27])=[CH:3][C:4]=3[N:8]=2)=[CH:14][CH:13]=1)([CH3:17])[CH3:16]

Participants

Conditions

Temperature: 180 °C

Procedure

A mixture of 430 mg (1.07 mmol) 5-bromo-2-(4-isopropyl-phenyl)-7-methoxy-1-(2-methoxy-ethyl)-1H-benzoimidazole (example 22), 125 mg (1.07 mmol) zinc cyanide and 20 mg tetrakis(triphenylphosphine) palladium in 5 ml DMF is heated in a microwave oven for 75 min (180° C.). After that the reaction mixture is poured on water and extracted (3×) with ethyl acetate. The combined organic layers are washed with water (3×) and brine, dried over MgSO4, filtered and concentrated in vacuo. The residue is purified by flash-chromatography on silica gel (hexane:EtOAc=3:1) to afford 250 mg of the title compound as a colorless solid.

Workup

additionAfter that the reaction mixture is poured on water
extractionextracted (3×) with ethyl acetate
washThe combined organic layers are washed with water (3×) and brine
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated in vacuo
customThe residue is purified by flash-chromatography on silica gel (hexane:EtOAc=3:1)

Sources & evidence

ORD record: ord-9269fb4d22f04ebc867f466114756382
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08030497B2

Reaction notes

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