Dimethylformamide → 5-Bromo-6-(2,4-difluorophenoxy)-1,3-dimethyl-1,3-dihydro-2H-benzimidazol-2-one

HRID 629309Notes

Reaction equation

[Br:1][C:2]1[C:11]([O:12][C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][C:14]=2[F:20])=[CH:10]C2N[C:7](=O)[NH:8][C:4]=2[CH:3]=1.[H-].[Na+].CI.[CH3:25][N:26]([CH3:29])[CH:27]=[O:28]>O>[Br:1][C:2]1[C:11]([O:12][C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][C:14]=2[F:20])=[CH:10][C:25]2[N:26]([CH3:29])[C:27](=[O:28])[N:8]([CH3:7])[C:4]=2[CH:3]=1

Participants

Conditions

Temperature: 20 °C

Procedure

A solution of 5-bromo-6-(2,4-difluorophenoxy)-1,3-dihydro-2H-benzimidazol-2-one (0.106 g, 0.311 mmol) in N,N-dimethylformamide (2.2 mL) was treated with sodium hydride (0.0273 g, 0.684 mmol) and stirred at 20° C. for 30 min. The reaction mixture was treated with methyl iodide (0.0426 mL, 0.684 mmol) and stirred 20° C. for 30 min. The reaction mixture was diluted with water which resulted in the formation of a precipitate. The solid was filtered and washed with water to give the desired product (108 mg, 94%) which was used without further purification. LCMS calculated for C15H12BrF2N2O2 (M+H)+: m/z=369.0, 371.0. found: 368.9, 371.0.

Workup

stirringstirred 20° C. for 30 min
customresulted in the formation of a precipitate
filtrationThe solid was filtered
washwashed with water

Sources & evidence

ORD record: ord-68b921bb8164476c9f1d32b58d535453
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09315501B2

Reaction notes

Loading…