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

Cesium carbonate → Ethyl 4-bromo-5-(3-cyano-5-fluorophenyl)thiophene-2-carboxylate

HRID 1037003
노트
인쇄 미리보기

반응식

HRID 1037003 반응식
[Br:1][C:2]1[CH:3]=[C:4]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[S:5][C:6]=1Br.[F:13][C:14]1[CH:15]=[C:16]([C:29]#[N:30])[CH:17]=[C:18](B2OC(C)(C)C(C)(C)O2)[CH:19]=1.C(=O)([O-])[O-].[Cs+].[Cs+].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1>COCCOC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[Br:1][C:2]1[CH:3]=[C:4]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[S:5][C:6]=1[C:18]1[CH:19]=[C:14]([F:13])[CH:15]=[C:16]([C:29]#[N:30])[CH:17]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 4

HCID 10796Cesium carbonateHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 15073982Ethyl 4,5-dibromothiophene-2-carboxylateHCID 467381943-Fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile

생성물 1

HCID 66681595Ethyl 4-bromo-5-(3-cyano-5-fluorophenyl)thiophene-2-carboxylate수율 62%

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 962Water용매HCID 80711,2-Dimethoxyethane용매

반응 조건

온도
50 °C

실험 절차

Under argon, 1.50 g (4.78 mmol) of the compound from Example 8A are provided in 75 ml of 1,2-dimethoxyethane, and 1.30 g (5.26 mmol) of the compound from Example 5A, 4.67 g (14.3 mmol) of cesium carbonate, 159 mg (0.33 mmol) of dicyclohexyl[2′,4′,6′-tri(propan-2-yl)biphenyl-2-yl]phosphane and 32.0 mg (0.14 mmol) of palladium(II) acetate are added. The mixture is stirred at 50° C. overnight. Water is subsequently added, the mixture is extracted with ethyl acetate and the extract is dried over sodium sulfate, filtered and concentrated. The crude product is purified by preparative HPLC (RP18 column; eluent: acetonitrile/water gradient with addition of 0.1% formic acid). 1.05 g of ethyl 4-bromo-5-(3-cyano-5-fluorophenyl)thiophene-2-carboxylate are obtained.

후처리

  1. extractionthe mixture is extracted with ethyl acetate
  2. dry with materialthe extract is dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude product is purified by preparative HPLC (RP18 column; eluent: acetonitrile/water gradient with addition of 0.1% formic acid)

출처 및 근거

ORD 기록
ord-36c8904c00114acba6b34c82c31a60ec
출처 데이터셋
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08546438B2

반응 노트

불러오는 중…

이 페이지에서참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트