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1,2-Dichloroethane → 2-[2-(4-Methoxyphenyl)ethyl]-N-methyl-N-[(1-methyl-1H-indol-2-yl)methyl]nicotinamide

HRID 1581684
ノート
印刷プレビュー

反応式

HRID 1581684 の反応式
C(Cl)CCl.[CH3:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][C:15]2[N:23]=[CH:22][CH:21]=[CH:20][C:16]=2[C:17]([OH:19])=O)=[CH:9][CH:8]=1.[CH3:24][N:25]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:27]=[C:26]1[CH2:34][NH:35][CH3:36].C1C=CC2N(O)N=NC=2C=1.C(N(C(C)C)CC)(C)C>CN(C=O)C.O>[CH3:5][O:6][C:7]1[CH:8]=[CH:9][C:10]([CH2:13][CH2:14][C:15]2[N:23]=[CH:22][CH:21]=[CH:20][C:16]=2[C:17]([N:35]([CH3:36])[CH2:34][C:26]2[N:25]([CH3:24])[C:33]3[C:28]([CH:27]=2)=[CH:29][CH:30]=[CH:31][CH:32]=3)=[O:19])=[CH:11][CH:12]=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 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 11401058methyl((1-methyl-1H-indol-2-yl)methyl)amineHCID 121253972-[2-(4-Methoxyphenyl)ethyl]nicotinic acid

生成物 1

HCID 99315542-[2-(4-Methoxyphenyl)ethyl]-N-methyl-N-[(1-methyl-1H-indol-2-yl)methyl]nicotinamide
収率 90.2%

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 6228Dimethylformamide溶媒

実験手順

EDC (0.60 g, 3.16 mmole) was added to a solution of 2-[2-(4-methoxyphenyl)ethyl]nicotinic acid (0.81 g, 3.16 mmole), 1-methyl-2-(methylaminomethyl)indole (0.50 g, 2.87 mmole), HOBt.H2O (0.43 g, 3.16 mmole), and diisopropylethylamine (0.55 mL, 3.16 mmole) in DMF (15 mL) at RT. The reaction was stirred overnight, then was diluted with H2O and extracted with EtOAc. Drying (Na2SO4), concentration, and flash chromatography on silica gel (5% MeOH/CHCl3) gave the title compound (1.07 g, 90%) as a viscous yellow oil: 1H NMR (300 MHz, DMSO-d6) δ 8.63 (m, 1H), 7.22-7.61 (m, 8H), 6.97 (d, J=8.1 Hz, 1H), 6.63 (d, J=8.1 Hz, 1H), 6.52 (s, 1H), 3.80 (s, 3H), 3.78 (m, 2H), 3.72 (s, 2H), 3.16 (m, 2H), 3.03 (s, 3H), 2.57 (s, 3H), MS (ES) m/e 414 (M+H)+. Anal. Calcd for C26H27N3O2: C, 75.52; H, 6.58: N, 10.16. Found C, 75.84; H, 6.68; N, 9.76.

後処理

  1. customat RT
  2. extractionextracted with EtOAc
  3. customDrying
  4. concentration(Na2SO4), concentration, and flash chromatography on silica gel (5% MeOH/CHCl3)

出典と根拠

ORDレコード
ord-fb9f71c9dafb43c99233e436fb20ca94
出典データセット
uspto-grants-2004_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06730684B1

反応ノート

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