Dimethylformamide → HCID 22349297, compound

HRID 896335Notes

Reaction equation

Br[C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[C:8]([CH2:10][OH:11])[N:7]([CH2:12][CH2:13][CH:14]([CH3:16])[CH3:15])[C:6]=2[CH:17]=1.[CH3:18][N:19](C=O)C>CO.[C-]#N.[C-]#N.[Zn+2].[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>[OH:11][CH2:10][C:8]1[N:7]([CH2:12][CH2:13][CH:14]([CH3:16])[CH3:15])[C:6]2[CH:17]=[C:2]([C:18]#[N:19])[CH:3]=[CH:4][C:5]=2[N:9]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of [6-bromo-1-(3-methyl-butyl)-1H-benzoimidazol-2-yl]-methanol (30 mg, 0.1 mmol), Zn(CN)2 (7 mg, 0.06 mmol) and tetrakis(triphenylphosphine) palladium(0) (12 mg, 0.01 mmol) in DMF (1 mL) was heated to 80° C. for 4 h. After cooling, the reaction mixture was diluted with MeOH and filtered. The filtrate was purified by prep-HPLC (gradient 10%-100% B) to give 16 mg (66%) of 2-hydroxymethyl-3-(3-methyl-butyl)-3H-benzoimidazole-5-carbonitrile as a white solid.

Workup

temperatureAfter cooling
filtrationfiltered
customThe filtrate was purified by prep-HPLC (gradient 10%-100% B)

Sources & evidence

ORD record: ord-1838766f180047b8bfb7cd6489972cd8
Source dataset: uspto-grants-2005_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06919331B2

Reaction notes

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