Dimethylformamide → HCID 178498261, compound

HRID 392205Notes

Reaction equation

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

Participants

Conditions

Temperature: 100 °C

Procedure

A solution of methyl 2-(4-bromobenzyl)-7-methoxy-3H-benzimidazole-4-carboxylate [1.4 g, Reference Example 3(1)] in dry dimethylformamide was treated with tetrakis(triphenylphosphine) palladium (0) (0.266 g) and zinc cyanide (0.275 g). The reaction mixture was heated at 100° C. for 12 hours then cooled to room temperature. The mixture was diluted with ethyl acetate and then washed with ammonium hydroxide (2N), then with water and then with brine. The organic solution was dried over magnesium sulphate then evaporated. The residue was subjected to flash chromatography on silica to give the title compound (0.88 g). NMR (CDCl3): δ 3.85(s, 3H), 4.00(s, 3H), 4.40(s, 2H), 6.70(d, 1H), 7.40(d, 2H), 7.65(d, 2H), 7.85(1H).

Workup

temperaturethen cooled to room temperature
washwashed with ammonium hydroxide (2N)
dry with materialThe organic solution was dried over magnesium sulphate
customthen evaporated

Sources & evidence

ORD record: ord-7128d904bfac4ae79fb6a7032a2dc799
Source dataset: uspto-grants-2004_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06800645B1

Reaction notes

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