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

HRID 629295Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]([NH2:18])[C:5]([NH2:17])=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][C:10]=1[F:16].C1N=CN([C:24](N2C=NC=C2)=[O:25])C=1>C(OCC)(=O)C>[Br:1][C:2]1[C:7]([O:8][C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][C:10]=2[F:16])=[CH:6][C:5]2[NH:17][C:24](=[O:25])[NH:18][C:4]=2[CH:3]=1

Participants

Conditions

Temperature: 50 °C

Procedure

A solution of 4-bromo-5-(2,4-difluorophenoxy)benzene-1,2-diamine (0.371 g, 1.18 mmol) in ethyl acetate (5.20 mL) was treated with N,N-carbonyldiimidazole (0.23 g, 1.4 mmol) and stirred at 50° C. for 30 min. The reaction mixture was treated with additional N,N-carbonyldiimidazole (1.2 eq) and stirred at 50° C. for 1 h. The reaction mixture was cooled to 20° C. and the heterogeneous mixture was filtered to give the desired product (156 mg, 39%) as a light grey solid. LCMS calculated for C13H8BrF2N2O2 (M+H)+: m/z=341.0, 343.0. found: 341.0, 342.9.

Workup

stirringstirred at 50° C. for 1 h
temperatureThe reaction mixture was cooled to 20° C.
filtrationthe heterogeneous mixture was filtered

Sources & evidence

ORD record: ord-c1d26d6cfcb74444942ccb70b51f5a20
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09315501B2

Reaction notes

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