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

Water → 5-bromo-N-methyl-6-(N-methylmethylsulfonamido)-2-(6-(trifluoromethyl)pyridin-3-yl)benzofuran-3-carboxamide

HRID 595642
노트
인쇄 미리보기

반응식

HRID 595642 반응식
[Br:1][C:2]1[C:3]([N:16]([CH3:21])[S:17]([CH3:20])(=[O:19])=[O:18])=[CH:4][C:5]2[O:9][C:8](I)=[C:7]([C:11]([NH:13][CH3:14])=[O:12])[C:6]=2[CH:15]=1.[F:22][C:23]([F:34])([F:33])[C:24]1[N:29]=[CH:28][C:27](B(O)O)=[CH:26][CH:25]=1.C([O-])([O-])=O.[Na+].[Na+].O>O1CCOCC1.O.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]>[Br:1][C:2]1[C:3]([N:16]([CH3:21])[S:17]([CH3:20])(=[O:19])=[O:18])=[CH:4][C:5]2[O:9][C:8]([C:27]3[CH:28]=[N:29][C:24]([C:23]([F:34])([F:33])[F:22])=[CH:25][CH:26]=3)=[C:7]([C:11]([NH:13][CH3:14])=[O:12])[C:6]=2[CH:15]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 251342782-(Trifluoromethyl)pyridine-5-boronic AcidHCID 903324695-bromo-2-iodo-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide

생성물 1

HCID 903324615-bromo-N-methyl-6-(N-methylmethylsulfonamido)-2-(6-(trifluoromethyl)pyridin-3-yl)benzofuran-3-carboxamide수율 90%

시약·촉매·용매

2
HCID 44119782Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 218864351,4-Dioxane--water (1/1)용매

반응 조건

온도
80 °C

실험 절차

A mixture of 5-bromo-2-iodo-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide (1.5 g, 3.1 mmol), (6-(trifluoromethyl)pyridin-3-yl)boronic acid (705 mg, 3.7 mmol), Pd(dppf)Cl2 (245 mg, 0.3 mmol) and Na2CO3 (985 mg, 9.3 mmol) in dioxane/H2O (20 mL/4 mL) was stirred at 80° C. for 6 h. Water was added and the mixture was extracted with EtOAc. The organic phase was dried over Na2SO4 and concentrated in vacuum. The residue was purified by column chromatography (PE:EA=1:1) to give the product of 5-bromo-N-methyl-6-(N-methylmethylsulfonamido)-2-(6-(trifluoromethyl)pyridin-3-yl)benzofuran-3-carboxamide (1.4 g, yield: 90%). 1H-NMR (DMSO-d6, 400 MHz) δ 9.24 (s, 1H), 8.65 (d, J=4.4 Hz, 1H), 8.56 (d, J=8.0 Hz, 1H), 8.17 (s, 1H), 8.12 (d, J=8.0 Hz, 1H), 8.08 (s, 1H), 3.23 (s, 3H), 3.22 (s, 3H), 2.85 (d, J=4.4 Hz, 3H). MS (M+H)+: 506/508.

후처리

  1. extractionthe mixture was extracted with EtOAc
  2. dry with materialThe organic phase was dried over Na2SO4
  3. concentrationconcentrated in vacuum
  4. customThe residue was purified by column chromatography (PE:EA=1:1)

출처 및 근거

ORD 기록
ord-84623478031c4bfb9f4f6bc255473170
출처 데이터셋
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09243002B2

반응 노트

불러오는 중…

이 페이지에서참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트