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Pyridine → HCID 58565348, 화합물

HRID 2175332
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HRID 2175332 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 37.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Activated molecular sieves (13 g) 4 Å were placed in an oven dried round bottom flask and cooled to room temperature under nitrogen. To the flask was charged with N-methoxy-N-methyl-1H-indole-2-carboxamide (0.97 g, 4.7 mmol), (3-fluorophenyl)-boronic acid (1.5 g, 11 mmol), cupric acetate (1.3 g, 7.3 mmol), methylene chloride (130 mL) and then pyridine (1.5 mL, 19 mmol). The reaction mixture was stirred at room temperature over the weekend. The mixture was filtered through a pad of Celite. The filtrate was concentrated and purified on silica gel (eluting with 0-30% EtOAc/hexane) to give the title compound (0.52 g, 37%). LCMS calculated for C17H16FN2O2(M+H)+: m/z=299.1. Found: 299.1.

후처리

  1. customActivated molecular sieves (13 g) 4 Å were placed in an oven
  2. customdried round bottom flask
  3. filtrationThe mixture was filtered through a pad of Celite
  4. concentrationThe filtrate was concentrated
  5. custompurified on silica gel (eluting with 0-30% EtOAc/hexane)

출처 및 근거

ORD 기록
ord-48430188543a4e988e2787475bc4030f
출처 데이터셋
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09062055B2

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