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Acetic Anhydride → N-(1-acetyl-2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-4-ylmethyl)-acetamide

HRID 887648
ノート
印刷プレビュー

反応式

HRID 887648 の反応式
[C:1]([N:4]1[C:8]2[N:9]=[CH:10][CH:11]=[C:12]([C:13]#[N:14])[C:7]=2[CH:6]=[CH:5]1)(=[O:3])[CH3:2].CCN(CC)CC.[C:22](OC(=O)C)(=[O:24])[CH3:23]>[Pd].CCOC(C)=O>[C:1]([N:4]1[C:8]2=[N:9][CH:10]=[CH:11][C:12]([CH2:13][NH:14][C:22](=[O:24])[CH3:23])=[C:7]2[CH2:6][CH2:5]1)(=[O:3])[CH3:2]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 219614211-Acetyl-1H-pyrrolo[2,3-b]pyridine-4-carbonitrile

生成物 1

HCID 21961391N-(1-acetyl-2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-4-ylmethyl)-acetamide

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 8857Ethyl Acetate
溶媒

実験手順

To a mixture of 1-acetyl-1H-pyrrolo[2,3-b]pyridine-4-carbonitrile (0.691 g, example 15, step D), 10% Pd/C (0.702 g), 5 mL of Et3N, and 20 mL of EtOAc was added acetic anhydride (1.0 mL). The mixture was stirred at RT under balloon pressure of H2 for overnight. Solid was removed by filtration through a pad of Celite® and the filtrate was concentrated to yield a white residue, which was purified by chromatography through silica gel (150 g, 1 to 5% MeOH/CHCl3 with 1% NH4OH, stepwise gradient) to afford N-(1-acetyl-2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-4-ylmethyl)-acetamide (0.50 g) as white solid.

後処理

  1. customSolid was removed by filtration through a pad of Celite®
  2. concentrationthe filtrate was concentrated
  3. customto yield a white residue, which
  4. customwas purified by chromatography through silica gel (150 g, 1 to 5% MeOH/CHCl3 with 1% NH4OH, stepwise gradient)

出典と根拠

ORDレコード
ord-2d66c9f6de51406087ac7b65c9337f3b
出典データセット
uspto-grants-2012_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08247430B2

反応ノート

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