Water → 2-Propen-1-yl {3-[bromo(2-chloro-4-pyrimidinyl)acetyl]-2-fluorophenyl}carbamate

HRID 1671228Notes

Reaction equation

[Cl:1][C:2]1[N:7]=[C:6]([CH2:8][C:9]([C:11]2[C:12]([F:24])=[C:13]([NH:17][C:18](=[O:23])[O:19][CH2:20][CH:21]=[CH2:22])[CH:14]=[CH:15][CH:16]=2)=[O:10])[CH:5]=[CH:4][N:3]=1.C1C(=O)N([Br:32])C(=O)C1.O>CC(N(C)C)=O>[Br:32][CH:8]([C:6]1[CH:5]=[CH:4][N:3]=[C:2]([Cl:1])[N:7]=1)[C:9]([C:11]1[C:12]([F:24])=[C:13]([NH:17][C:18](=[O:23])[O:19][CH2:20][CH:21]=[CH2:22])[CH:14]=[CH:15][CH:16]=1)=[O:10]

Participants

Conditions

Temperature: 25 °C

Procedure

To a stirring mixture of 2-propen-1-yl {3-[(2-chloro-4-pyrimidinyl)acetyl]-2-fluorophenyl}carbamate (5 g, 14.30 mmol) in DMA (100 ml) was added NBS (2.54 g, 14.30 mmol) and mixture was stirred at 25° C. overnight. The reaction mixture was poured into water (400 ml) and extracted with EtOAc (100 ml×3). The combined organic layers were dried over Na2SO4 and evaporated to afford the title compound as a yellow oil (6.1 g, 99%). MS (ES): 427 [M+H]+.

Workup

extractionextracted with EtOAc (100 ml×3)
dry with materialThe combined organic layers were dried over Na2SO4
customevaporated

Sources & evidence

ORD record: ord-a695e5dfda64414aa0af4f738aa89a86
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07994185B2

Reaction notes

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