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

Cesium carbonate → ethyl (2E)-3-(6-{[(3R)-1-(4-chlorobenzoyl)-3-pyrrolidinyl]amino}-3-pyridyl)acrylate

HRID 2376034
노트
인쇄 미리보기

반응식

HRID 2376034 반응식
Cl[C:2]1[N:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[Cl:21][C:22]1[CH:35]=[CH:34][C:25]([C:26]([N:28]2[CH2:32][CH2:31][C@@H:30]([NH2:33])[CH2:29]2)=[O:27])=[CH:24][CH:23]=1>O1CCOCC1.CCOC(C)=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(N(C)C)=CC=CC=2)CCCCC1>[Cl:21][C:22]1[CH:35]=[CH:34][C:25]([C:26]([N:28]2[CH2:32][CH2:31][C@@H:30]([NH:33][C:2]3[N:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][CH:3]=3)[CH2:29]2)=[O:27])=[CH:24][CH:23]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 3

HCID 10796Cesium carbonateHCID 108461873-(6-Chloro-pyridin-3-yl)-acrylic acid ethyl esterHCID 68963176(3R)-1-(4-chlorobenzoyl)-3-pyrrolidinamine

생성물 1

HCID 86603659ethyl (2E)-3-(6-{[(3R)-1-(4-chlorobenzoyl)-3-pyrrolidinyl]amino}-3-pyridyl)acrylate수율 32.7%

시약·촉매·용매 4

HCID 167845palladium(II) acetate
촉매
HCID 27342172-(Dicyclohexylphosphino)-2'-(dimethylamino)biphenyl촉매
HCID 8857Ethyl Acetate용매
HCID 312751,4-Dioxane용매

반응 조건

온도
90 °C

실험 절차

To a solution of ethyl (2E)-3-(6-chloro-3-pyridyl)acrylate (3.5 g) in dioxane (70 mL) was added palladium(II) acetate (371 mg) and 2′-(dicyclohexylphosphino)-N,N-dimethyl-2-biphenylamine (110 mg) and cesium carbonate (583 mg), and (3R)-1-(4-chlorobenzoyl)-3-pyrrolidinamine (4.09 g). The mixture was heated at 90° C. for 3 hours. The resulting mixture was diluted with AcOEt, and the precipitate was removed by filtration. The filtrate was concentrated and residual brown oil was purified by purified by silica gel column chromatography eluted with AcOEt and hexane (1:4)-AcOEt to give ethyl (2E)-3-(6-{[(3R)-1-(4-chlorobenzoyl)-3-pyrrolidinyl]amino}-3-pyridyl)acrylate (2.16 g) as dark yellow form.

후처리

  1. customthe precipitate was removed by filtration
  2. concentrationThe filtrate was concentrated
  3. customresidual brown oil was purified
  4. customby purified by silica gel column chromatography
  5. washeluted with AcOEt and hexane (1:4)-AcOEt

출처 및 근거

ORD 기록
ord-095b240c2a4d4283ac372fc039136bbf
출처 데이터셋
uspto-grants-2008_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07465731B2

반응 노트

불러오는 중…

이 페이지에서참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트