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

HRID 1690382

反応式

HRID 1690382 の反応式
[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

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 6228Dimethylformamide溶媒HCID 7854Propionitrile溶媒

実験手順

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)+.

後処理

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

出典と根拠

ORDレコード
ord-73240552b55c4c0a81b58a0d81e33871
出典データセット
uspto-grants-2012_04
特許番号
US08153652B2

関連ノート

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