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Pyridine → HCID 58565348, 화합물

HRID 2175325
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HRID 2175325 반응식
[CH3:1][O:2][N:3]([CH3:15])[C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:5].[F:16][C:17]1[CH:18]=[C:19](B(O)O)[CH:20]=[CH:21][CH:22]=1.N1C=CC=CC=1>C(Cl)Cl>[F:16][C:17]1[CH:22]=[C:21]([N:7]2[C:8]3[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=3)[CH:14]=[C:6]2[C:4]([N:3]([O:2][CH3:1])[CH3:15])=[O:5])[CH:20]=[CH:19][CH:18]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 1049PyridineHCID 27339863-Fluorophenylboronic acidHCID 11095718N-methoxy-N-methyl-1H-indole-2-carboxamide

생성물 1

HCID 58565348HCID 58565348, 화합물수율 46%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Activated molecular sieves (6.0 g) 4 Å were placed in an oven dried flask and cooled to room temperature under nitrogen. To the flask was charged with N-methoxy-N-methyl-1H-indole-2-carboxamide (0.45 g, 2.2 mmol), (3-fluorophenyl)boronic acid (0.94 g, 6.7 mmol), cupric acetate (0.60 g, 3.3 mmol), and methylene chloride (80 mL) and then pyridine (0.72 mL, 8.9 mmol). The reaction mixture was stirred at room temperature over weekend, then filtered through a pad of Celite. The filtrate was concentrated and purified on silica gel (eluting with 0-25% EtOAc in hexane) to give the title compound (0.30 g, 46%). LCMS calculated for C17H16FN2O2(M+H)+: m/z=299.1. Found: 299.0.

후처리

  1. customActivated molecular sieves (6.0 g) 4 Å were placed in an oven
  2. customdried flask
  3. filtrationfiltered through a pad of Celite
  4. concentrationThe filtrate was concentrated
  5. custompurified on silica gel (eluting with 0-25% EtOAc in hexane)

출처 및 근거

ORD 기록
ord-0b90f261049c4840b09469fd30752940
출처 데이터셋
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09062055B2

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