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

HRID 1661947Notes

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]C)[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.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[OH:20][CH2:19][CH2:18][N:6]1[C:5]2[C:22]([O:24][CH3:25])=[CH:23][C:2]([C:26]#[N:27])=[CH:3][C:4]=2[N:8]=[C:7]1[C:9]1[CH:10]=[CH:11][C:12]([CH:15]([CH3:16])[CH3:17])=[CH:13][CH:14]=1

Participants

Conditions

Temperature: 180 °C

Procedure

A solution of 1.42 g (3.52 mmol) of 5-Bromo-2-(4-isopropyl-phenyl)-7-methoxy-1-(2-methoxy-ethyl)-1H-benzoimidazole and 455 mg (3.87 mmol) zinc cyanide in 15 ml DMF is stirred under argon for 10 min at RT. Tetrakis(triphenylphosphine)palladium (214 mg, 0.176 mmol) is added and the reaction is heated to 180° C. for 90 min. After cooling to RT, ice/water is added and the reaction mixture is extracted with ethyl acetate (3×). The organic layer is washed with water, dried (Na2SO4) and concentrated in vacuo and the material is used without further purification.

Workup

temperatureAfter cooling to RT
extractionthe reaction mixture is extracted with ethyl acetate (3×)
washThe organic layer is washed with water
dry with materialdried (Na2SO4)
concentrationconcentrated in vacuo
customthe material is used without further purification

Sources & evidence

ORD record: ord-35ebe1f0b957477890ce768ee7e9d952
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08030497B2

Reaction notes

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