4-[(E)-2-(2,6-dichloro-4-morpholin-4-yl-phenyl)-vinyl]-3-nitrobenzoic acid methyl ester → 2-(2,6-dichloro-4-morpholin-4-yl-phenyl)-1H-indole-6-carboxylic acid methyl ester

HRID 1514951ノート

反応式

HRID 1514951 の反応式
[CH3:1][O:2][C:3](=[O:29])[C:4]1[CH:9]=[CH:8][C:7](/[CH:10]=[CH:11]/[C:12]2[C:17]([Cl:18])=[CH:16][C:15]([N:19]3[CH2:24][CH2:23][O:22][CH2:21][CH2:20]3)=[CH:14][C:13]=2[Cl:25])=[C:6]([N+:26]([O-])=O)[CH:5]=1>C(OP(OCC)OCC)C>[CH3:1][O:2][C:3]([C:4]1[CH:5]=[C:6]2[C:7]([CH:10]=[C:11]([C:12]3[C:17]([Cl:18])=[CH:16][C:15]([N:19]4[CH2:24][CH2:23][O:22][CH2:21][CH2:20]4)=[CH:14][C:13]=3[Cl:25])[NH:26]2)=[CH:8][CH:9]=1)=[O:29]

参加物

3

反応物 1

HCID 669662594-[(E)-2-(2,6-dichloro-4-morpholin-4-yl-phenyl)-vinyl]-3-nitrobenzoic acid methyl ester

生成物 1

HCID 669658232-(2,6-dichloro-4-morpholin-4-yl-phenyl)-1H-indole-6-carboxylic acid methyl ester

試薬・触媒・溶媒 1

HCID 31215Triethyl phosphite溶媒

反応条件

温度
160 °C

実験手順

A suspension of 4-[(E)-2-(2,6-dichloro-4-morpholin-4-yl-phenyl)-vinyl]-3-nitrobenzoic acid methyl ester (1.25 g, 2.86 mmol) in triethylphosphite (10 mL) was heated at 160° C. for 1 h. The mixture was concentrated under reduced pressure and the residue was triturated to afford 2-(2,6-dichloro-4-morpholin-4-yl-phenyl)-1H-indole-6-carboxylic acid methyl ester as a light yellow solid. 1H NMR (400 MHz, DMSO-d6) δ 11.72 (d, J=1.52 Hz, 1H), 8.02 (d, J=1.01 Hz, 1H), 7.64 (s, 2H), 7.15 (s, 2H), 6.53 (dd, J=1.96, 0.82 Hz, 1H), 3.86 (s, 3H), 3.70-3.76 (m, 4H), 3.25-3.30 (m, 4H). MS (m/z) 405.1 (M+1).

後処理

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customthe residue was triturated

出典と根拠

ORDレコード
ord-6519755e52844388a12424e3569dd6c5
出典データセット
uspto-grants-2012_07
特許番号
US08222248B2

反応ノート

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