Potassium Carbonate → N-(3-Methoxybenzyl)-5-(1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)thiophene-3-carboxamide

HRID 2108755ノート

反応式

HRID 2108755 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:16]=[CH:17][CH:18]=1)[CH2:6][NH:7][C:8]([C:10]1[CH:14]=[C:13](Br)[S:12][CH:11]=1)=[O:9].CC1(C)C(C)(C)OB([C:27]2[C:35]3[C:30](=[N:31][CH:32]=[CH:33][CH:34]=3)[N:29]([S:36]([C:39]3[CH:45]=[CH:44][C:42]([CH3:43])=[CH:41][CH:40]=3)(=[O:38])=[O:37])[CH:28]=2)O1.C(=O)([O-])[O-].[K+].[K+]>COCCOC.CCOC(C)=O.O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:16]=[CH:17][CH:18]=1)[CH2:6][NH:7][C:8]([C:10]1[CH:14]=[C:13]([C:27]2[C:35]3[C:30](=[N:31][CH:32]=[CH:33][CH:34]=3)[N:29]([S:36]([C:39]3[CH:45]=[CH:44][C:42]([CH3:43])=[CH:41][CH:40]=3)(=[O:38])=[O:37])[CH:28]=2)[S:12][CH:11]=1)=[O:9]

参加物

8

反応物 3

HCID 11430Potassium CarbonateHCID 497589593-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridineHCID 57421982N-(3-Methoxybenzyl)-5-bromothiophene-3-carboxamide

生成物 1

HCID 57633172N-(3-Methoxybenzyl)-5-(1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)thiophene-3-carboxamide収率 45%

試薬・触媒・溶媒 4

HCID 11979704Tetrakis(triphenylphosphine)palladium触媒HCID 962Water溶媒2 回HCID 80711,2-Dimethoxyethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

N-(3-Methoxybenzyl)-5-bromothiophene-3-carboxamide (100 mg, 0.3 mmol), 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine (122 mg, 0.3 mmol), potassium carbonate (125 mg, 0.9 mmol), and tetrakis(triphenylphosphine) palladium (0) (20 mg) were combined in 4 mL DME, 1 mL water, and heated to 160° C. in the microwave for 10 minutes. The reaction mixture was diluted with EtOAc and water. The organic layer was filtered through celite and concentrated to an oil which was purified by column chromatography on silica (20 to 60% EtOAc/hexanes) to give the product as a brown oil, 0.07 g, 0.14 mmol, 45% yield. MH+ 518.0

後処理

  1. filtrationThe organic layer was filtered through celite
  2. concentrationconcentrated to an oil which
  3. customwas purified by column chromatography on silica (20 to 60% EtOAc/hexanes)

出典と根拠

ORDレコード
ord-802ff1787b58405e8e331d338c9c74da
出典データセット
uspto-grants-2009_04
特許番号
US07514448B2

反応ノート

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