4-Bromo-2-methoxy-6-methylaniline → Methyl 2-[(4-bromo-2-methoxy-6-methylphenyl)amino]-1-methyl-1H-benzimidazole-7-carboxylate

HRID 2235574Notes

Reaction equation

Cl[C:2]1[N:6]([CH3:7])[C:5]2[C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:9][CH:10]=[CH:11][C:4]=2[N:3]=1.[Br:16][C:17]1[CH:22]=[C:21]([CH3:23])[C:20]([NH2:24])=[C:19]([O:25][CH3:26])[CH:18]=1>ClCCl>[Br:16][C:17]1[CH:22]=[C:21]([CH3:23])[C:20]([NH:24][C:2]2[N:6]([CH3:7])[C:5]3[C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:9][CH:10]=[CH:11][C:4]=3[N:3]=2)=[C:19]([O:25][CH3:26])[CH:18]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 1.50 g (6.68 mmol) of methyl 2-chloro-1-methyl-1H-benzimidazole-7-carboxylate and 2.89 g (13.4 mmol) of 4-bromo-2-methoxy-6-methylphenylamine was heated at 100° C. for five days. The cooled reaction was dissolved in dichloromethane and washed with saturated aqueous sodium bicarbonate, water and brine. The organics were dried over sodium sulfate, filtered, and concentrated in vacuo. The thus obtained residue was purified via flash chromatography eluting with 100% dichloromethane to elute the residual 4-bromo-2-methoxy-6-methylphenylamine and 30% ethyl acetate/hexanes to give 356 mg (13%) of the title compound.

Workup

customThe cooled reaction
washwashed with saturated aqueous sodium bicarbonate, water and brine
dry with materialThe organics were dried over sodium sulfate
filtrationfiltered
concentrationconcentrated in vacuo
customThe thus obtained residue was purified via flash chromatography
washeluting with 100% dichloromethane
washto elute the residual 4-bromo-2-methoxy-6-methylphenylamine and 30% ethyl acetate/hexanes

Sources & evidence

ORD record: ord-0d4215888b3a490990dbe7b0482889b3
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07714009B2

Reaction notes

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