N,N'-Dimethylethylenediamine → 1-(4-Isopropoxyphenyl)-5-(6-isopropoxypyrid-3-yl)indole-2-carb-oxylic acid ethyl ester

HRID 646105ノート

反応式

HRID 646105 の反応式
CNCCNC.[CH2:7]([O:9][C:10]([C:12]1[NH:13][C:14]2[C:19]([CH:20]=1)=[CH:18][C:17]([C:21]1[CH:22]=[N:23][C:24]([O:27][CH:28]([CH3:30])[CH3:29])=[CH:25][CH:26]=1)=[CH:16][CH:15]=2)=[O:11])[CH3:8].Br[C:32]1[CH:37]=[CH:36][C:35]([O:38][CH:39]([CH3:41])[CH3:40])=[CH:34][CH:33]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>[Cu]I.C1(C)C=CC=CC=1>[CH2:7]([O:9][C:10]([C:12]1[N:13]([C:32]2[CH:37]=[CH:36][C:35]([O:38][CH:39]([CH3:41])[CH3:40])=[CH:34][CH:33]=2)[C:14]2[C:19]([CH:20]=1)=[CH:18][C:17]([C:21]1[CH:22]=[N:23][C:24]([O:27][CH:28]([CH3:29])[CH3:30])=[CH:25][CH:26]=1)=[CH:16][CH:15]=2)=[O:11])[CH3:8]

参加物

7

反応物 4

HCID 8070N,N'-DimethylethylenediamineHCID 62657Potassium Phosphate, TribasicHCID 2280881-Bromo-4-(propan-2-yloxy)benzeneHCID 686994605-(6-Isopropoxypyrid-3-yl)indole-2-carboxylic acid ethyl ester

生成物 1

HCID 686982341-(4-Isopropoxyphenyl)-5-(6-isopropoxypyrid-3-yl)indole-2-carb-oxylic acid ethyl ester収率 70%

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 1140Toluene溶媒2 回

反応条件

温度
140 °C

実験手順

A mixture of CuI (7.14 mg, 51 mmol), N,N′-dimethyl-1,2-diaminoethane (16.7 μL, 0.153 mmol) and toluene (0.5 mL) was added to a mixture of 5-(6-isopropoxypyrid-3-yl)indole-2-carboxylic acid ethyl ester (165 mg, 0.510 mmol; see step (a)), 1-bromo-4-isopropoxybenzene (219 mg, 1.02 mmol), K3PO4 (108 mg, 0.510 mmol) and toluene (2 mL) under argon. The mixtures was heated at 110° C. for 5 h and at 140° C. for 16 h, then allowed to cool to room temperature and filtered through Celite®. The filter cake was washed with EtOAc and the combined filtrates were concentrated and purified by chromatography to give the sub-title compound (163 mg, 70%).

後処理

  1. temperatureto cool to room temperature
  2. filtrationfiltered through Celite®
  3. washThe filter cake was washed with EtOAc
  4. concentrationthe combined filtrates were concentrated
  5. custompurified by chromatography

出典と根拠

ORDレコード
ord-74250d38cf034607bba27150bbd648bc
出典データセット
uspto-grants-2010_04
特許番号
US07705023B2

反応ノート

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