2-Bromo-3'-chloro-4'-fluoroacetophenone → 4-[4-(3-Chloro-4-fluoro-phenyl)-thiazol-2-yl]-2'-nitro-biphenyl-2-carboxylic acid methyl ester

HRID 1519273Notes

Reaction equation

Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([F:11])=[C:7]([Cl:12])[CH:6]=1)=O.[CH3:13][O:14][C:15]([C:17]1[C:18]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[N+:32]([O-:34])=[O:33])=[CH:19][CH:20]=[C:21]([C:23](=[S:25])[NH2:24])[CH:22]=1)=[O:16]>C1COCC1>[CH3:13][O:14][C:15]([C:17]1[C:18]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[N+:32]([O-:34])=[O:33])=[CH:19][CH:20]=[C:21]([C:23]2[S:25][CH:2]=[C:3]([C:5]3[CH:10]=[CH:9][C:8]([F:11])=[C:7]([Cl:12])[CH:6]=3)[N:24]=2)[CH:22]=1)=[O:16]

Participants

Conditions

Temperature: 40 °C

Procedure

2-Bromo-3′-chloro-4′-fluoroacetophenone (available from Aldrich Chemical Company, Inc.; 80.5 mg, 0.32 mmol) was added to a solution of 2′-nitro-4-thiocarbamoyl-biphenyl-2-carboxylic acid methyl ester (which may be prepared as described for Intermediate 4; 100 mg, 0.32 mmol) in THF (2 mL), and the resulting mixture was stirred at 40° C. for 20 h. The reaction mixture was evaporated to dryness and the residue was stirred with ethanol (5 mL). The precipitate was collected by filtration (100 mg) and used directly in the next step without purification.

Workup

customThe reaction mixture was evaporated to dryness
stirringthe residue was stirred with ethanol (5 mL)
filtrationThe precipitate was collected by filtration (100 mg)
customused directly in the next step without purification

Sources & evidence

ORD record: ord-032f764b273d4e42ab468111fd59258b
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09073881B2

Reaction notes

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