dimethyl 2-((1-(4-fluorophenyl)-1H-indazol-5-yl)methylene)malonate → dimethyl 2-((1-(4-fluorophenyl)-1H-indazol-5-yl)(phenyl)methyl)malonate

HRID 563436노트

반응식

HRID 563436 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([CH:17]=[C:18]([C:23]([O:25][CH3:26])=[O:24])[C:19]([O:21][CH3:22])=[O:20])=[CH:14][CH:15]=3)[CH:10]=[N:9]2)=[CH:4][CH:3]=1.[C:27]1([Mg]Br)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>C1COCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([CH:17]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[CH:18]([C:23]([O:25][CH3:26])=[O:24])[C:19]([O:21][CH3:22])=[O:20])=[CH:14][CH:15]=3)[CH:10]=[N:9]2)=[CH:4][CH:3]=1

참가 물질

4

반응물 2

HCID 67005843dimethyl 2-((1-(4-fluorophenyl)-1H-indazol-5-yl)methylene)malonateHCID 178418255HCID 178418255, 화합물

생성물 1

HCID 59252807dimethyl 2-((1-(4-fluorophenyl)-1H-indazol-5-yl)(phenyl)methyl)malonate수율 84%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

Dimethyl 2-((1-(4-fluorophenyl)-1H-indazol-5-yl)methylene)malonate (424 mg, 1.2 mmol) was dissolved in 10 mL dry THF and 1.0M phenylmagnesium bromide in THF (5 mL, 5.0 mmol) was added. The reaction mixture was stirred for 12 h. The reaction was quenched with MeOH then poured into brine and extracted with EtOAc×3. The organic layers were dried over MgSO4, filtered, and concentrated. The residue was purified on SiO2 by MPLC and eluting with 1:3 EtOAc/hexane. Obtained 435 mg (84% yield) of dimethyl 2-((1-(4-fluorophenyl)-1H-indazol-5-yl)(phenyl)methyl)malonate. MS found: (M+H)+=333.

후처리

  1. customThe reaction was quenched with MeOH
  2. additionthen poured into brine
  3. extractionextracted with EtOAc×3
  4. dry with materialThe organic layers were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified on SiO2 by MPLC
  8. washeluting with 1:3 EtOAc/hexane

출처 및 근거

ORD 기록
ord-f85b1c9818964def9cdd63e54c4a9a6c
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08067447B2

반응 노트

불러오는 중…