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

Triethylamine → 4-(6-Cyano-pyridin-3-yloxy)-2,2-dimethyl-2,3-dihydro-benzofuran-6-carboxylic acid (1-methyl-1H-pyrazol-3-yl)-amide

HRID 1643635
노트
인쇄 미리보기

반응식

HRID 1643635 반응식
CC1(C)C(C)(C)OB([C:9]2[CH:10]=[CH:11][C:12]([C:15]#[N:16])=[N:13][CH:14]=2)O1.[CH3:18][N:19]1[CH:23]=[CH:22][C:21]([NH:24][C:25]([C:27]2[CH:37]=[C:36]([OH:38])[C:30]3[CH2:31][C:32]([CH3:35])([CH3:34])[O:33][C:29]=3[CH:28]=2)=[O:26])=[N:20]1.CCN(CC)CC>C(Cl)Cl.CC([O-])=O.CC([O-])=O.[Cu+2]>[CH3:18][N:19]1[CH:23]=[CH:22][C:21]([NH:24][C:25]([C:27]2[CH:37]=[C:36]([O:38][C:9]3[CH:14]=[N:13][C:12]([C:15]#[N:16])=[CH:11][CH:10]=3)[C:30]3[CH2:31][C:32]([CH3:35])([CH3:34])[O:33][C:29]=3[CH:28]=2)=[O:26])=[N:20]1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 164141882-Cyanopyridine-5-boronic acid pinacol esterHCID 595600842,3-Dihydro-4-hydroxy-2,2-dimethyl-N-(1-methyl-1H-pyrazol-3-yl)-6-benzofurancarboxamide

생성물 1

HCID 667561004-(6-Cyano-pyridin-3-yloxy)-2,2-dimethyl-2,3-dihydro-benzofuran-6-carboxylic acid (1-methyl-1H-pyrazol-3-yl)-amide수율 47.5%

시약·촉매·용매 2

HCID 8895
Cupric acetate
촉매
HCID 6344Dichloromethane용매

실험 절차

A mixture of 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinonitrile (634 mg, 2.76 mmol), 4-hydroxy-2,2-dimethyl-2,3-dihydro-benzofuran-6-carboxylic acid (1-methyl-1H-pyrazol-3-yl)-amide (31a) (396 mg, 1.33 mmol), Et3N (0.96 mL, 6.89 mmol), and Cu(OAc)2 (501 mg, 2.76 mmol) in CH2Cl2 (15 mL) was stirred at room temperature with 4 A molecular sieves for 4 days, then filtered through celite, washed with CHCl3, concentrated, and purified by column chromatography with 30-60% EtOAc in hexanes to give a white foam (246 mg, 46% yield). 1H NMR (400 MHz, CDCl3) δ 9.23 (s, 1 H) 8.45 (d, J=2.53 Hz, 1 H) 7.65 (d, J=8.59 Hz, 1 H) 7.21-7.35 (m, 2H) 7.10 (d, J=11.37 Hz, 2 H) 6.78 (d, J=2.02 Hz, 1 H) 3.73 (s, 3 H) 2.89 (s, 2 H)) 1.48 (s, 6 H); LCMS for C21H19N5O3 m/z 390.00 (M+H+).

후처리

  1. filtrationfiltered through celite
  2. washwashed with CHCl3
  3. concentrationconcentrated
  4. custompurified by column chromatography with 30-60% EtOAc in hexanes

출처 및 근거

ORD 기록
ord-a71d43fffbfd4030b4914ae271b0d270
출처 데이터셋
uspto-grants-2012_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08119624B2

반응 노트

불러오는 중…

이 페이지에서참가 물질실험 절차후처리출처 및 근거반응 노트