Tributylphosphine → Methyl(4-chloro-7-fluoro-6-((2-methyl-6-(trifluoromethyl)pyridin-3-yl)methoxy)-1-benzothiophen-3-yl)acetate

HRID 591461노트

반응식

HRID 591461 반응식
C(P(CCCC)CCCC)CCC.[CH3:14][O:15][C:16](=[O:30])[CH2:17][C:18]1[C:22]2[C:23]([Cl:29])=[CH:24][C:25]([OH:28])=[C:26]([F:27])[C:21]=2[S:20][CH:19]=1.[CH3:31][C:32]1[C:37]([CH2:38]O)=[CH:36][CH:35]=[C:34]([C:40]([F:43])([F:42])[F:41])[N:33]=1.C1CCN(C(N=NC(N2CCCCC2)=O)=O)CC1>C1COCC1>[CH3:14][O:15][C:16](=[O:30])[CH2:17][C:18]1[C:22]2[C:23]([Cl:29])=[CH:24][C:25]([O:28][CH2:38][C:37]3[C:32]([CH3:31])=[N:33][C:34]([C:40]([F:43])([F:41])[F:42])=[CH:35][CH:36]=3)=[C:26]([F:27])[C:21]=2[S:20][CH:19]=1

참가 물질

6

반응물 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 2760122(2-Methyl-6-(trifluoromethyl)pyridin-3-yl)methanolHCID 121006517Methyl 2-(4-chloro-7-fluoro-6-hydroxy-1-benzothiophen-3-yl)acetate

생성물 1

HCID 118667010Methyl(4-chloro-7-fluoro-6-((2-methyl-6-(trifluoromethyl)pyridin-3-yl)methoxy)-1-benzothiophen-3-yl)acetate수율 91%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a mixture of tri-n-butylphosphine (0.264 mL), methyl(4-chloro-7-fluoro-6-hydroxy-1-benzothiophen-3-yl)acetate (116 mg), (2-methyl-6-(trifluoromethyl)pyridin-3-yl)methanol (89 mg) and THF (4.0 mL) was added ADDP (213 mg) at room temperature. The mixture was stirred at room temperature under nitrogen atmosphere for 1 h. The mixture was concentrated in vacuo. To the residue was added IPE and the precipitate was filtered off. The filtrate was concentrated in vacuo. The residue was purified by silica gel column chromatography (NH, EtOAc/hexane) to give the title compound (172 mg).

후처리

  1. concentrationThe mixture was concentrated in vacuo
  2. additionTo the residue was added IPE
  3. filtrationthe precipitate was filtered off
  4. concentrationThe filtrate was concentrated in vacuo
  5. customThe residue was purified by silica gel column chromatography (NH, EtOAc/hexane)

출처 및 근거

ORD 기록
ord-086d3c0f17774deeaa9d901c6bc01225
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09238639B2

반응 노트

불러오는 중…