Sodium hydride → 2-[4-(Diphenylmethoxy)phenyl]-1-cyclohexyl-1H-benzimidazole-5-carbonitrile

HRID 392960Notes

Reaction equation

[H-].[Na+].[OH:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:14]([CH:15]3[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]3)[C:13]3[CH:21]=[CH:22][C:23]([C:25]#[N:26])=[CH:24][C:12]=3[N:11]=2)=[CH:6][CH:5]=1.[H][H].[C:29]1([CH:35](Br)[C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>CN(C=O)C.O>[C:29]1([CH:35]([C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=2)[O:3][C:4]2[CH:9]=[CH:8][C:7]([C:10]3[N:14]([CH:15]4[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]4)[C:13]4[CH:21]=[CH:22][C:23]([C:25]#[N:26])=[CH:24][C:12]=4[N:11]=3)=[CH:6][CH:5]=2)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

Conditions

Temperature: 55 °C

Procedure

A 60% dispersion of sodium hydride in mineral oil (50 mg, 1.25 mmol) was added in a single portion to a stirred mixture of compound 6 in DMF (3.5 mL). When the rapid evolution of hydrogen had ceased, the mixture was cooled in an ice-water bath. Diphenylmethyl bromide (297 mg, 1.2 mmol) was added. The mixture was stirred at an oil bath temperature of 55° C. for 30 min. The mixture was cooled and poured into cold water to precipitate a solid. The solid was dried and crystallized from ethyl acetate-hexanes to afford 8 as off white needles. ESI-MS m/e 484 (M+1).

Workup

temperaturethe mixture was cooled in an ice-water bath
temperatureThe mixture was cooled
customto precipitate a solid
customThe solid was dried
customcrystallized from ethyl acetate-hexanes
customto afford 8 as off white needles

Sources & evidence

ORD record: ord-bec5b9e659b741abadd27e7470c318c4
Source dataset: uspto-grants-2004_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06803374B2

Reaction notes

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