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

Dichloromethane → 5-{4-[3-(2-Fluoro-5-methyl-phenylcarbamoyl)-phenoxy]-pyridin-2-yl}-1H-pyrrole-3-carboxylic acid methyl ester

HRID 521776
노트
인쇄 미리보기

반응식

HRID 521776 반응식
Br[C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:10]=[C:11]([CH:23]=[CH:24][CH:25]=2)[C:12]([NH:14][C:15]2[CH:20]=[C:19]([CH3:21])[CH:18]=[CH:17][C:16]=2[F:22])=[O:13])[CH:5]=[CH:4][N:3]=1.CC1(C)C(C)(C)OB([C:34]2[NH:38][CH:37]=[C:36]([C:39]([O-:41])=[O:40])[CH:35]=2)O1.[CH2:43](Cl)Cl>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:43][O:41][C:39]([C:36]1[CH:35]=[C:34]([C:2]2[CH:7]=[C:6]([O:8][C:9]3[CH:25]=[CH:24][CH:23]=[C:11]([C:12](=[O:13])[NH:14][C:15]4[CH:20]=[C:19]([CH3:21])[CH:18]=[CH:17][C:16]=4[F:22])[CH:10]=3)[CH:5]=[CH:4][N:3]=2)[NH:38][CH:37]=1)=[O:40]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 6344DichloromethaneHCID 581678683-(2-bromo-pyridin-4-yloxy)-N-(2-fluoro-5-methyl-phenyl)-benzamideHCID 866515565-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrole-3-carboxylate

생성물 1

HCID 510016275-{4-[3-(2-Fluoro-5-methyl-phenylcarbamoyl)-phenoxy]-pyridin-2-yl}-1H-pyrrole-3-carboxylic acid methyl ester수율 2,806.2%

시약·촉매·용매 1

HCID 44119782
Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)
촉매

반응 조건

온도
95 °C

실험 절차

A mixture of 3-(2-bromo-pyridin-4-yloxy)-N-(2-fluoro-5-methyl-phenyl)-benzamide (200 mg, 0.50 mmol), methyl-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrole-3-carboxylate (251 mg, 1.0 mmol) and PdCl2(dppf).CH2Cl2 (10 mg, 0.012 mmol) was added to a thick-walled reaction vessel and purged with N2. A solution of 2M Na2CO3 (0.5 mL) was added, followed by DMSO (8 mL). The reaction vessel was sealed and the mixture stirred at 95° C. for 16 h. The reaction vessel was cooled to room temperature and the mixture was poured into 100 ml of water. The precipitates were filtered, washed with water and dried to give the crude, which was purified via column chromatography eluting with 30-40% EtOAc/hexanes to afford 5-{4-[3-(2-Fluoro-5-methyl-phenylcarbamoyl)-phenoxy]-pyridin-2-yl}-1H-pyrrole-3-carboxylic acid methyl ester (150 mg, 58% yield).

후처리

  1. custompurged with N2
  2. additionA solution of 2M Na2CO3 (0.5 mL) was added
  3. customThe reaction vessel was sealed
  4. temperatureThe reaction vessel was cooled to room temperature
  5. additionthe mixture was poured into 100 ml of water
  6. filtrationThe precipitates were filtered
  7. washwashed with water
  8. customdried
  9. customto give the crude, which
  10. customwas purified via column chromatography
  11. washeluting with 30-40% EtOAc/hexanes

출처 및 근거

ORD 기록
ord-dcb608e4832641a497643cd16d278e14
출처 데이터셋
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09328103B2

반응 노트

불러오는 중…

이 페이지에서참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트