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

HRID 659142노트

반응식

HRID 659142 반응식
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]

참가 물질

4

반응물 2

HCID 967492-Bromo-1-(4-fluorophenyl)ethan-1-one2회HCID 343747Ethyl 2-amino-4-methylthiazole-5-carboxylate

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

반응 조건

온도
95 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-2d1a042126cf4c5fbc6093d23e1ea0d4
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08080569B2

반응 노트

불러오는 중…