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

1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) → Carbamic acid, N-[1-(6-hydroxy-3-quinolinyl)-3-pyrrolidinyl]-, 1,1-dimethylethyl ester

HRID 2175136
노트
인쇄 미리보기

반응식

HRID 2175136 반응식
C([O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[N:11]=[CH:10][C:9](Br)=[CH:8]2)(=O)C.[NH:16]1[CH2:20][CH2:19][CH:18]([NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[CH2:17]1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.CC([O-])(C)C.[K+]>CN(C=O)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[OH:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[N:11]=[CH:10][C:9]([N:16]1[CH2:20][CH2:19][CH:18]([NH:21][C:22](=[O:28])[O:23][C:24]([CH3:26])([CH3:25])[CH3:27])[CH2:17]1)=[CH:8]2
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 2757234tert-butyl N-(pyrrolidin-3-yl)carbamateHCID 23665647Potassium tert-butoxideHCID 685300473-Bromoquinolin-6-yl acetate

생성물 1

HCID 86696256Carbamic acid, N-[1-(6-hydroxy-3-quinolinyl)-3-pyrrolidinyl]-, 1,1-dimethylethyl ester수율 12%

시약·촉매·용매 2

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 6228Dimethylformamide용매

반응 조건

온도
110 °C

실험 절차

A mixture of Intermediate A (1.50 g, 5.07 mmol), tert-butyl pyrrolidin-3-ylcarbamate (1.13 g, 6.09 mmol), Pd2(dba)3 (0.232 g, 0.254 mmol), Xantphos (0.294 g, 0.507 mmol) and KOtBu (1.14 g, 10.2 mmol) in DMF (15 mL) was bubbled with argon for 20 min. The result mixture was heated at 110° C. overnight. The solution was cooled to rt and the solvent was removed under reduced pressure. The residue was diluted with water, extracted with DCM three times. The combined organic phase was dried over anhydrous Na2SO4, filtered and concentrated. The crude product was purified by chromatography (eluting with 5% MeOH in DCM) to give the title compound as yellow solid (0.2 g, yield 11%). LCMS (method N): [M+H]+=330, tR=1.93 min.

후처리

  1. customwas bubbled with argon for 20 min
  2. temperatureThe solution was cooled to rt
  3. customthe solvent was removed under reduced pressure
  4. additionThe residue was diluted with water
  5. extractionextracted with DCM three times
  6. dry with materialThe combined organic phase was dried over anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude product was purified by chromatography (eluting with 5% MeOH in DCM)

출처 및 근거

ORD 기록
ord-dc9dd3fcf64d4589bb1e0468547c6b64
출처 데이터셋
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09062045B2

반응 노트

불러오는 중…

이 페이지에서참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트