Water → 2-(5-Bromo-2,3-dihydro-1H-indol-1-yl)-1H-benzimidazole

HRID 573277

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH2:6][CH2:5]2.Cl[C:12]1[NH:16][C:15]2[CH:17]=[CH:18][CH:19]=[CH:20][C:14]=2[N:13]=1.O>CC(N(C)C)=O.CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([C:12]1[NH:16][C:15]3[CH:17]=[CH:18][CH:19]=[CH:20][C:14]=3[N:13]=1)[CH2:6][CH2:5]2

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of 5-bromoindoline (1 g) and 2-chloro-1H-benzo[d]imidazole (0.770 g) in DMA/DMF (5 mL, 3/2) was stirred at 150° C. for 12 h, treated with water, and extracted with AcOEt. The organic layer was dried over MgSO4 and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (AcOEt/hexane) to give the title compound (1.1 g).

Workup

extractionextracted with AcOEt
dry with materialThe organic layer was dried over MgSO4
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel column chromatography (AcOEt/hexane)

Sources & evidence

ORD record: ord-382a041251144bd1a58a76f565fcab9f
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09029536B2

Linked notes

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