Cesium carbonate → 2-{4-[(4'-Chloro-4-methoxy-1,1'-biphenyl-2-yl)methoxy]phenyl}-1-cyclohexyl-1H-benzimidazole-5-carbonitrile

HRID 392965Notes

Reaction equation

[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH:13]3[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]3)[C:11]3[CH:19]=[CH:20][C:21]([C:23]#[N:24])=[CH:22][C:10]=3[N:9]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:32][C:33]1[CH:38]=[C:37]([O:39][CH3:40])[CH:36]=[CH:35][C:34]=1[C:41]1[CH:46]=[CH:45][C:44]([Cl:47])=[CH:43][CH:42]=1>CN(C=O)C>[Cl:47][C:44]1[CH:43]=[CH:42][C:41]([C:34]2[CH:35]=[CH:36][C:37]([O:39][CH3:40])=[CH:38][C:33]=2[CH2:32][O:1][C:2]2[CH:7]=[CH:6][C:5]([C:8]3[N:12]([CH:13]4[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]4)[C:11]4[CH:19]=[CH:20][C:21]([C:23]#[N:24])=[CH:22][C:10]=4[N:9]=3)=[CH:4][CH:3]=2)=[CH:46][CH:45]=1

Participants

Conditions

Temperature: 40 °C

Procedure

A suspension of compound 6 (0.330 g, 1.04 mmol) in DMF (2.4 mL) and cesium carbonate (339 mg, 1.04 mmol) was heated at 40° C. until almost clear. Compound 14 (356 mg, 1.14 mmol) was added in portions. The reaction mixture was stirred at rt for 18 h. The mixture was concentrated on a rotary evaporator. The residue was washed with water and collected by filtration. This material was purified by column chromatography (silica gel, 50% to 100% hexane/ethyl acetate (v/v) to give compound 15 (0.55 g, 100% yield). ESI-MS m/e 548 (M=1).

Workup

concentrationThe mixture was concentrated on a rotary evaporator
washThe residue was washed with water
filtrationcollected by filtration
customThis material was purified by column chromatography (silica gel, 50% to 100% hexane/ethyl acetate (v/v)

Sources & evidence

ORD record: ord-73d7d6cb08804a92981c527b9495bb7e
Source dataset: uspto-grants-2004_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06803374B2

Reaction notes

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