Tri-o-tolylphosphine → (E)-3-(2-aminopyrimidin-5-yl)-N-(2-methyl-1H-indol-3-ylmethyl)-N-methylacrylamide

HRID 1297438

반응식

HRID 1297438 반응식
[CH3:1][N:2]([CH2:7][C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[NH:10][C:9]=1[CH3:17])[C:3](=[O:6])[CH:4]=[CH2:5].[NH2:18][C:19]1[N:24]=[CH:23][C:22](Br)=[CH:21][N:20]=1.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(N(C(C)C)CC)(C)C>C(#N)CC.CN(C=O)C.CC([O-])=O.CC([O-])=O.[Pd+2]>[NH2:18][C:19]1[N:24]=[CH:23][C:22](/[CH:5]=[CH:4]/[C:3]([N:2]([CH2:7][C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[NH:10][C:9]=2[CH3:17])[CH3:1])=[O:6])=[CH:21][N:20]=1

참가 물질

8

반응물 4

HCID 80271Tri-o-tolylphosphineHCID 81531DiisopropylethylamineHCID 2313102-Amino-5-bromopyrimidineHCID 22139057N-(2-methyl-1H-indol-3-ylmethyl)-N-methylacrylamide

생성물 1

HCID 9973366(E)-3-(2-aminopyrimidin-5-yl)-N-(2-methyl-1H-indol-3-ylmethyl)-N-methylacrylamide수율 128.8%

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 6228Dimethylformamide용매HCID 7854Propionitrile용매

실험 절차

A solution of N-methyl-N-(2-methyl-1H-indol-3-ylmethyl)acrylamide (1.18 g, 6.5 mmole), 2-amino-5-bromopyrimidine (0.5 g, 2.9 mmole), Pd(OAc)2 (0.11 g, 0.49 mmole), tri-ortho-tolylphosphine (0.17 g, 0.55 mmole), and diisopropylethylamine (1.5 mL, 8.6 mmole) in propionitrile (100 mL) and DMF (10 mL) was heated at reflux overnight. The dark mixture was filtered through celite®, and the filtrate was concentrated. Flash chromatography on silica gel (9:1 CHCl3/CH3OH containing 5% NH4OH) gave the title compound (1.2 g, 65%): MS (ES) m/e 372 (M+H)+.

후처리

  1. temperatureat reflux overnight
  2. filtrationThe dark mixture was filtered through celite®
  3. concentrationthe filtrate was concentrated

출처 및 근거

ORD 기록
ord-847b775e0a8c4f029b2aded48a3e58fe
출처 데이터셋
uspto-grants-2007_07
특허 번호
US07250424B2

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