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

Cesium carbonate → Ethyl 5-[2-(acetylamino)pyridin-4-yl]-2-bromo-3-furoate

HRID 537034
노트
인쇄 미리보기

반응식

HRID 537034 반응식
[Br:1][C:2]1[O:3][C:4](Br)=[CH:5][C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8].CC1(C)C(C)(C)OB([C:21]2[CH:26]=[CH:25][N:24]=[C:23]([NH:27][C:28](=[O:30])[CH3:29])[CH:22]=2)O1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:28]([NH:27][C:23]1[CH:22]=[C:21]([C:4]2[O:3][C:2]([Br:1])=[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH:5]=2)[CH:26]=[CH:25][N:24]=1)(=[O:30])[CH3:29]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 3

HCID 10796Cesium carbonateHCID 49760417N-(4-(tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)acetamideHCID 53216927Ethyl 2,5-dibromofuran-3-carboxylate

생성물 1

HCID 66748312Ethyl 5-[2-(acetylamino)pyridin-4-yl]-2-bromo-3-furoate수율 14%

시약·촉매·용매 3

HCID 11979704
Tetrakis(triphenylphosphine)palladium
촉매
HCID 962Water용매2회
HCID 312751,4-Dioxane용매

실험 절차

To a solution of ethyl 2,5-dibromo-3-furoate (0.21 g, 0.722 mmol) in 1,4-dioxane (2.2 mL) and water (0.50 mL) were added tetrakis(triphenylphosphine) palladium(0) (0.08 g, 0.07 mmol), N-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl]acetamide (0.19 g, 0.72 mmol) and cesium carbonate (0.71 g, 2.2 mmol). The reaction mixture was subjected to microwave irradiation at 95° C. for 15 min. The reaction mixture was diluted with water (10 mL) and extracted with EtOAc. The organic solutions were combined, washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified by column chromatography to give ethyl 5-[2-(acetylamino)pyridin-4-yl]-2-bromo-3-furoate (0.035 g, 14%) as a white solid. LCMS (FA): m/z=339.1 (M+H).

후처리

  1. customirradiation at 95° C. for 15 min
  2. extractionextracted with EtOAc
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography

출처 및 근거

ORD 기록
ord-15b71ea8d78444dea49ff0abc2951521
출처 데이터셋
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08859768B2

반응 노트

불러오는 중…

이 페이지에서참가 물질실험 절차후처리출처 및 근거반응 노트