Cesium carbonate → HCID 24801837、化合物

HRID 883168ノート

反応式

HRID 883168 の反応式
[CH2:1]([CH:8]1[CH2:12][NH:11][C:10](=[O:13])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:14]([NH:21][C:22]([C:24]1[S:28][C:27](Br)=[N:26][C:25]=1[CH3:30])=[O:23])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH2:14]([NH:21][C:22]([C:24]1[S:28][C:27]([N:11]2[CH2:12][CH:8]([CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH2:9][C:10]2=[O:13])=[N:26][C:25]=1[CH3:30])=[O:23])[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

参加物

7

反応物 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 187848954-Benzylpyrrolidin-2-oneHCID 579593962-Bromo-4-methyl-thiazole-5-carboxylic acid benzylamide

生成物 1

HCID 24801837HCID 24801837、化合物収率 13.1%

試薬・触媒・溶媒 2

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 1140Toluene溶媒

実験手順

A mixture of 4-benzylpyrrolidin-2-one (0.068 g, 0.39 mmol), N-benzyl-2-bromo-4-methylthiazole-5-carboxamide (0.10 g, 0.32 mmol), cesium carbonate (0.16 g, 0.48 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.006 g, 0.060 mmol) and xantphos (0.008 g, 0.013 mmol) in anhydrous toluene (3 mL) was subjected to microwave irradiation at 120° C. for 15 min. The reaction mixture was concentrated in vacuo and the residue was purified by column chromatography (ethyl acetate/hexanes (1/1)) to afford the title compound as a white solid (0.017 g, 13%): mp 143-144° C. (hexanes/ethyl acetate); 1H NMR (300 MHz, CDCl3) δ 7.38-7.11 (m, 10H), 5.91 (br s, 1H), 4.56 (d, J=5.5 Hz, 2H), 4.25-4.13 (m, 1H), 3.85-3.72 (m, 1H), 2.95-2.68 (m, 4H), 2.61 (s, 3H), 2.52-2.39 (m, 1H); 13C NMR (75 MHz, CDCl3) δ 173.0, 162.3, 155.3, 152.6, 138.2, 137.9, 128.8, 128.7, 127.9, 127.6, 126.8, 118.6, 52.6, 44.0, 40.1, 37.7, 33.4, 17.2; MS (ES+) m/z 406.3 (M+1).

後処理

  1. customirradiation at 120° C. for 15 min
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customthe residue was purified by column chromatography (ethyl acetate/hexanes (1/1))

出典と根拠

ORDレコード
ord-ecfa5bab102a40788284b7a89009ec70
出典データセット
uspto-grants-2012_08
特許番号
US08236835B2

反応ノート

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