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

Methanol → 4-(2-Chloro-5-methylpyridin-4-yl)-1-(2,4,6-trimethylbenzensulfonyl)-1H-pyrrole-2-carboxylic acid methyl ester

HRID 2374136
노트
인쇄 미리보기

반응식

HRID 2374136 반응식
[CH3:1][O:2][C:3]([C:5]1[N:6]([S:19]([C:22]2[C:27]([CH3:28])=[CH:26][C:25]([CH3:29])=[CH:24][C:23]=2[CH3:30])(=[O:21])=[O:20])[CH:7]=[C:8](B2OC(C)(C)C(C)(C)O2)[CH:9]=1)=[O:4].Br[C:32]1[C:37]([CH3:38])=[CH:36][N:35]=[C:34]([Cl:39])[CH:33]=1.CO.C([O-])([O-])=O.[Na+].[Na+]>C1C=CC=CC=1.C(OCC)(=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:1][O:2][C:3]([C:5]1[N:6]([S:19]([C:22]2[C:27]([CH3:28])=[CH:26][C:25]([CH3:29])=[CH:24][C:23]=2[CH3:30])(=[O:20])=[O:21])[CH:7]=[C:8]([C:32]2[C:37]([CH3:38])=[CH:36][N:35]=[C:34]([Cl:39])[CH:33]=2)[CH:9]=1)=[O:4]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 4

HCID 887MethanolHCID 10340Sodium CarbonateHCID 534399184-Bromo-2-chloro-5-methylpyridineHCID 59767810Methyl 1-(mesitylsulfonyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrole-2-carboxylate

생성물 1

HCID 866027194-(2-Chloro-5-methylpyridin-4-yl)-1-(2,4,6-trimethylbenzensulfonyl)-1H-pyrrole-2-carboxylic acid methyl ester수율 43.1%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 241Benzene용매HCID 8857Ethyl Acetate용매

실험 절차

4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-1-(2,4,6-trimethylbenzensulfonyl)-1H-pyrrole-2-carboxylic acid methyl ester (125 mg, 0.29 mmol, 0.6 equiv.) and 4-bromo-2-chloro-5-methylpyridine (96 mg, 0.47 mmol, 1.0 equiv.) were dissolved in benzene (4 mL). After adding methanol (0.94 mL) and aqueous Na2CO3, Pd(PPh3)4 (108 mg, 0.094 mol, 0.2 equiv.) was then added and the resulting mixture was heated at reflux for 16 hours. The reaction mixture was dissolved in ethyl acetate and washed with water. After drying the organic layer over Na2SO4, the solvent was removed under reduced pressure. The crude material was purified by reversed phase HPLC (acetonitrile/water/TFA), yielding the title compound as a colorless solid (54 mg, 0.125 mmol, HPLC Rt 9.087 min, ES+433.0, ES−431.0).

후처리

  1. additionwas then added
  2. temperaturethe resulting mixture was heated
  3. temperatureat reflux for 16 hours
  4. washwashed with water
  5. dry with materialAfter drying the organic layer over Na2SO4
  6. customthe solvent was removed under reduced pressure
  7. customThe crude material was purified by reversed phase HPLC (acetonitrile/water/TFA)

출처 및 근거

ORD 기록
ord-f7afad396acd4b7db3e143fbd08b8443
출처 데이터셋
uspto-grants-2008_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07462612B2

반응 노트

불러오는 중…

이 페이지에서참가 물질실험 절차후처리출처 및 근거반응 노트