1,2-Dichloroethane → (E)-N-methyl-N-(2-methyl-1H-indol-3-ylmethyl)-3-(2-oxo-2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-5-yl)acrylamide

HRID 1297439

反応式

HRID 1297439 の反応式
Cl.[O:2]=[C:3]1[CH2:11][C:10]2[C:5](=C[CH:7]=[C:8](/[CH:12]=[CH:13]/[C:14]([OH:16])=O)[CH:9]=2)[NH:4]1.O.OC1C2N=N[NH:24]C=2C=CC=1.C(N(C(C)C)CC)(C)C.[CH3:37][C:38]1[NH:39][C:40]2[C:45]([C:46]=1[CH2:47][NH:48][CH3:49])=[CH:44][CH:43]=[CH:42][CH:41]=2.C(Cl)CCl>CN(C=O)C>[CH3:49][N:48]([CH2:47][C:46]1[C:45]2[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=2)[NH:39][C:38]=1[CH3:37])[C:14](=[O:16])/[CH:13]=[CH:12]/[C:8]1[CH:9]=[C:10]2[CH2:11][C:3](=[O:2])[NH:4][C:5]2=[N:24][CH:7]=1

参加物

7

反応物 5

HCID 111,2-DichloroethaneHCID 81531DiisopropylethylamineHCID 10954023N-Methyl-N-[(2-methyl-1H-indol-3-yl)methyl]amineHCID 66905016(e)-3-(2-Oxo-2,3-dihydro-1h-indol-5-yl)acrylic acid hydrochloride saltHCID 178526939HCID 178526939、化合物

生成物 1

HCID 10021425(E)-N-methyl-N-(2-methyl-1H-indol-3-ylmethyl)-3-(2-oxo-2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-5-yl)acrylamide収率 88%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of (E)-3-(2-oxo-2,3-dihydro-1H-indol-5-yl)acrylic acid hydrochloride salt (0.50 g, 2.1 mmole), hydroxybenzotriazole monohydrate (0.31 g, 2.3 mmole), diisopropylethylamine (0.80 mL, 4.6 mmole), and 2-methyl-3-(methylaminomethyl)indole (0.40 g, 2.3 mmole) in DMF (50 mL) at RT was added EDC (0.46, 2.3 mmole). After 12 hr the reaction solution was concentrated under vacuum and the residue was purified by flash chromatography on silica gel (9:1 CHCl3/CH3OH containing 5% NH4OH) to give the title compound (0.66 g, 88%) as a light yellow solid: MS (ES) m/e 361 (M+H)+.

後処理

  1. concentrationAfter 12 hr the reaction solution was concentrated under vacuum
  2. customthe residue was purified by flash chromatography on silica gel (9:1 CHCl3/CH3OH containing 5% NH4OH)

出典と根拠

ORDレコード
ord-481e49e6a0434aaa97c42162fd970bd6
出典データセット
uspto-grants-2007_07
特許番号
US07250424B2

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