홈MCP워크벤치Skills
홈워크벤치알림마이페이지
llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
  1. 홈
  2. /반응

Cesium carbonate → (3r)-(3-Methoxy-pyrrolidin-1-yl)-[7-(2-methyl-1h-indol-5-yloxy)-thieno[3,2-b]pyridin-2-yl]-methanone

HRID 889882
노트
인쇄 미리보기

반응식

HRID 889882 반응식
C([O-])([O-])=O.[Cs+].[Cs+].Cl[C:8]1[CH:13]=[CH:12][N:11]=[C:10]2[CH:14]=[C:15]([C:17]([N:19]3[CH2:23][CH2:22][C@@H:21]([O:24][CH3:25])[CH2:20]3)=[O:18])[S:16][C:9]=12.[CH3:26][C:27]1[NH:28][C:29]2[C:34]([CH:35]=1)=[CH:33][C:32]([OH:36])=[CH:31][CH:30]=2>CN(C=O)C>[CH3:25][O:24][C@@H:21]1[CH2:22][CH2:23][N:19]([C:17]([C:15]2[S:16][C:9]3[C:10](=[N:11][CH:12]=[CH:13][C:8]=3[O:36][C:32]3[CH:33]=[C:34]4[C:29](=[CH:30][CH:31]=3)[NH:28][C:27]([CH3:26])=[CH:35]4)[CH:14]=2)=[O:18])[CH2:20]1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 833362-methyl-1H-indol-5-olHCID 207677657-chloro-2-[(R)-3-methoxypyrrolidine-1-carbonyl]thieno[3,2-b]pyridine

생성물 1

HCID 10223104(3r)-(3-Methoxy-pyrrolidin-1-yl)-[7-(2-methyl-1h-indol-5-yloxy)-thieno[3,2-b]pyridin-2-yl]-methanone수율 84%

시약·촉매·용매 1

HCID 6228Dimethylformamide
용매

반응 조건

온도
90 °C

실험 절차

Cs2CO3 (0.495 g, 1.52 mmol) was added to a solution of (3R)-(7-chloro-thieno[3,2-b]pyridin-2-yl)-(3-methoxy-pyrrolidin-1-yl)-methanone (0.228 g, 0.76 mmol) and 2-methyl-1H-indol-5-ol (0.223 9, 1.52 mmol) in DMF (5 mL), and the resulting solution was heated to 90° C. After 20 h the reaction was quenched with water, EtOAc was added, and the layers were separated. The aqueous layer was extracted with EtOAc, and the combined organic layers were dried over Na2SO4 then concentrated. The resulting material was purified on silica gel by flash column chromatography, eluting with CH2Cl2/MeOH (98/2) to afford the title compound as a white solid (0.26 g, 84%). MS: 408.8 (MH+); HPLC Rf: 5.394 min.; HPLC purity: 97%.

후처리

  1. customAfter 20 h the reaction was quenched with water, EtOAc
  2. additionwas added
  3. customthe layers were separated
  4. extractionThe aqueous layer was extracted with EtOAc
  5. dry with materialthe combined organic layers were dried over Na2SO4
  6. concentrationthen concentrated
  7. customThe resulting material was purified on silica gel by flash column chromatography
  8. washeluting with CH2Cl2/MeOH (98/2)

출처 및 근거

ORD 기록
ord-be1de9888ff34679a55b4e1e6369b7ef
출처 데이터셋
uspto-grants-2006_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06995171B2

반응 노트

불러오는 중…

이 페이지에서참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트