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1,2-Dichloroethane → (E)-3-(6-aminopyridin-3-yl)-N-(1H-indol-2-ylmethyl)-N-methylacrylamide

HRID 225926
ノート
印刷プレビュー

反応式

HRID 225926 の反応式
C(Cl)CCl.[NH2:5][C:6]1[N:11]=[CH:10][C:9]([CH:12]=[CH:13][C:14]([OH:16])=O)=[CH:8][CH:7]=1.[CH3:17][NH:18][CH2:19][C:20]1[NH:21][C:22]2[C:27]([CH:28]=1)=[CH:26][CH:25]=[CH:24][CH:23]=2.C1C=CC2N(O)N=NC=2C=1.O.C(N(C(C)C)CC)(C)C>CN(C=O)C>[NH2:5][C:6]1[N:11]=[CH:10][C:9](/[CH:12]=[CH:13]/[C:14]([N:18]([CH2:19][C:20]2[NH:21][C:22]3[C:27]([CH:28]=2)=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH3:17])=[O:16])=[CH:8][CH:7]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 6

HCID 111,2-DichloroethaneHCID 962WaterHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 11194490N-Methyl-1H-indole-2-methanamineHCID 534008323-(6-Aminopyridin-3-yl)prop-2-enoic acid

生成物 1

HCID 9861351
(E)-3-(6-aminopyridin-3-yl)-N-(1H-indol-2-ylmethyl)-N-methylacrylamide
収率 68.5%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

EDC (0.30 g, 1.58 mmole) was added to a solution of 3-(6-aminopyridin-3-yl)acrylic acid (0.26 g, 158 mmole), 2-(methylaminomethyl)-1H-indole (0.23 g, 1.43 mmole), HOBt.H2O (0.21 g, 1.58 mmole) and diisopropylethylamine (0.51 mL, 2.86 mmole) in DMF (20 mL) at RT. The reaction was stirred overnight, then was concentrated in vacuo. The residue was diluted with water and extracted with ethyl acetate. The combined organic extracts were washed with brine and dried over Na2SO4. Flash chromatography on silica gel (10% MeOH/CHCl3) gave the title compound (0.30 g. 68%) as a light yellow solid: MS (ES) m/e 307 (M+H)+.

後処理

  1. customat RT
  2. concentrationwas concentrated in vacuo
  3. additionThe residue was diluted with water
  4. extractionextracted with ethyl acetate
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried over Na2SO4

出典と根拠

ORDレコード
ord-c66f11b95426469f8897b2cbaa8bc877
出典データセット
uspto-grants-2009_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07557125B2

反応ノート

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