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

Toluene → 6-cyclopropyl-1-(toluene-4-sulfonyl)-1H-indole-2-carboxylic acid methyl ester

HRID 74459
노트
인쇄 미리보기

반응식

HRID 74459 반응식
[CH3:1][O:2][C:3]([C:5]1[N:6]([S:15]([C:18]2[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=2)(=[O:17])=[O:16])[C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[C:9](Br)[CH:8]=2)=[O:4].[CH3:25][C:26](P(C(C)(C)C)C1C=CC=CC=1)([CH3:28])C.C(=O)([O-])[O-].[Cs+].[Cs+].C1(C)C=CC=CC=1>C(OCC)(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[CH3:1][O:2][C:3]([C:5]1[N:6]([S:15]([C:18]2[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=2)(=[O:17])=[O:16])[C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[C:9]([CH:28]1[CH2:26][CH2:25]1)[CH:8]=2)=[O:4]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 4

HCID 1140TolueneHCID 10796Cesium carbonateHCID 316378Di-tert-butylphenylphosphineHCID 680048106-bromo-1-(toluene-4-sulfonyl)-1H-indole-2-carboxylic acid methyl ester

생성물 1

HCID 680048306-cyclopropyl-1-(toluene-4-sulfonyl)-1H-indole-2-carboxylic acid methyl ester

시약·촉매·용매 3

HCID 167845
palladium(II) acetate
촉매
HCID 962Water용매
HCID 8857Ethyl Acetate용매

반응 조건

온도
100 °C

실험 절차

Predetermined amounts of 6-bromo-1-(toluene-4-sulfonyl)-1H-indole-2-carboxylic acid methyl ester (300 mg, 0.73 mmol), palladium acetate (16.5 mg, 0.07 mmol), bis(1,1-dimethylethyl)phenylphosphine (0.028 ml, 0.12 mmol), potassium cyclopropyl trifluoroborate (163 mg, 1.1 mmol), and cesium carbonate (718 mg, 2.2 mmol) were placed in a reaction container, and toluene (5 ml) and water (0.5 ml) were added thereto. The resulting mixture was then stirred at 100° C. for 14 hours. After cooling it to room temperature, the mixture was diluted with ethyl acetate, and washed twice with water, and then dried over anhydrous sodium sulfate. The desiccant was removed by filtration, and concentration was performed. Then, the residue obtained by concentration under reduced pressure was purified by silica gel column chromatography (hexane/ethyl acetate=97/3 to 7/3). Thus, a yellow solid was obtained (208 mg, 77%).

후처리

  1. additionwere added
  2. temperatureAfter cooling it to room temperature
  3. washwashed twice with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe desiccant was removed by filtration, and concentration
  6. customThen, the residue obtained by concentration under reduced pressure
  7. customwas purified by silica gel column chromatography (hexane/ethyl acetate=97/3 to 7/3)
  8. customThus, a yellow solid was obtained (208 mg, 77%)

출처 및 근거

ORD 기록
ord-fb17bd2a5fb640e9b9ec8cb20bfeb4f5
출처 데이터셋
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08829199B2

반응 노트

불러오는 중…

이 페이지에서참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트