2-Bromo-1-(4-fluorophenyl)ethan-1-one → Ethyl 6-(4-fluorophenyl)-3-methylimidazo[2,1-b][1,3]thiazole-2-carboxylate

HRID 659142Notes

Reaction equation

Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][CH:6]=1)=O.[CH2:12]([O:14][C:15]([C:17]1[S:21][C:20]([NH2:22])=[N:19][C:18]=1[CH3:23])=[O:16])[CH3:13]>C(O)C>[CH2:12]([O:14][C:15]([C:17]1[S:21][C:20]2=[N:22][C:3]([C:5]3[CH:10]=[CH:9][C:8]([F:11])=[CH:7][CH:6]=3)=[CH:2][N:19]2[C:18]=1[CH3:23])=[O:16])[CH3:13]

Participants

Conditions

Temperature: 95 °C

Procedure

2-Bromo-1-(4-fluoro-phenyl)-ethanone (200 mg, 0.92 mmol) and 2-amino-4-methyl-thiazole-5-carboxylic acid ethyl ester (186.2 mg, 0.92 mmol) were heated in 5 ml of ethanol at 95° C. for 5 hours. After addition of 80 mg of 2-bromo-1-(4-fluoro-phenyl)-ethanone and further heating for 9 hours at 95° C. the mixture was evaporated. Addition of potassium hydrogensulfate solution, extraction with ethyl acetate and purification by preparative HPLC (RP18, acetonitrile/water 0.1% TFA) yielded 81 mg (32%) of the desired product. MS (mass spectrum): M+H+=305.07.

Workup

customwas evaporated
additionAddition of potassium hydrogensulfate solution, extraction
customwith ethyl acetate and purification by preparative HPLC (RP18, acetonitrile/water 0.1% TFA)

Sources & evidence

ORD record: ord-2d1a042126cf4c5fbc6093d23e1ea0d4
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08080569B2

Reaction notes

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