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

HRID 659142ノート

反応式

HRID 659142 の反応式
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]

参加物

4

反応物 2

HCID 967492-Bromo-1-(4-fluorophenyl)ethan-1-one2 回HCID 343747Ethyl 2-amino-4-methylthiazole-5-carboxylate

生成物 1

HCID 19224540Ethyl 6-(4-fluorophenyl)-3-methylimidazo[2,1-B]thiazole-2-carboxylate収率 32%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
95 °C

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-2d1a042126cf4c5fbc6093d23e1ea0d4
出典データセット
uspto-grants-2011_12
特許番号
US08080569B2

反応ノート

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