Ethanol → methyl 7-[4-(2-butoxyethoxy)phenyl]-1-(N-methyl4-sulfamoylphenyl)-2,3-dihydro-1H-1-benzazepine-4-carboxylate

HRID 586951ノート

反応式

HRID 586951 の反応式
Br[C:2]1[CH:3]=[CH:4][C:5]2[N:11]([C:12]3[CH:17]=[CH:16][C:15]([S:18](=[O:22])(=[O:21])[NH:19][CH3:20])=[CH:14][CH:13]=3)[CH2:10][CH2:9][C:8]([C:23]([O:25][CH3:26])=[O:24])=[CH:7][C:6]=2[CH:27]=1.B([O-])([O-])O[C:30]1[CH:35]=[CH:34][C:33]([O:36][CH2:37][CH2:38][O:39][CH2:40][CH2:41][CH2:42][CH3:43])=[CH:32][CH:31]=1.C(=O)([O-])[O-].[K+].[K+].C(O)C>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1(C)C=CC=CC=1>[CH2:40]([O:39][CH2:38][CH2:37][O:36][C:33]1[CH:32]=[CH:31][C:30]([C:2]2[CH:3]=[CH:4][C:5]3[N:11]([C:12]4[CH:17]=[CH:16][C:15]([S:18](=[O:21])(=[O:22])[NH:19][CH3:20])=[CH:14][CH:13]=4)[CH2:10][CH2:9][C:8]([C:23]([O:25][CH3:26])=[O:24])=[CH:7][C:6]=3[CH:27]=2)=[CH:35][CH:34]=1)[CH2:41][CH2:42][CH3:43]

参加物

7

反応物 4

HCID 702EthanolHCID 11430Potassium CarbonateHCID 22329309methyl 7-bromo-1-(N-methyl-4-sulfamoylphenyl)-2,3-dihydro-1H-1-benzazepine-4-carboxylateHCID 867568154-Butoxyethoxyphenyl borate

生成物 1

HCID 22329213methyl 7-[4-(2-butoxyethoxy)phenyl]-1-(N-methyl4-sulfamoylphenyl)-2,3-dihydro-1H-1-benzazepine-4-carboxylate収率 87.9%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 1140Toluene溶媒

実験手順

A mixture of methyl 7-bromo-1-(N-methyl-4-sulfamoylphenyl)-2,3-dihydro-1H-1-benzazepine-4-carboxylate (1 g), 4-(2-butoxyethoxy)phenyl borate (0.69 g), 1M potassium carbonate solution (8 ml), ethanol (8 ml) and toluene (100 ml) was stirred under argon atmosphere at room temperature for 30 minutes. To the mixture was added tetrakis(triphenylphosphine)palladium (0.13 g), and the mixture was refluxed under argon atmosphere for 2.5 hours and extracted with ethyl acetate. The organic layer was washed with water and saturated brine and dried with anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified with silica gel column chromatography (ethyl acetate/hexane) to give methyl 7-[4-(2-butoxyethoxy)phenyl]-1-(N-methyl4-sulfamoylphenyl)-2,3-dihydro-1H-1-benzazepine-4-carboxylate (1.1 g) as colorless crystals.

後処理

  1. temperaturethe mixture was refluxed under argon atmosphere for 2.5 hours
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water and saturated brine
  4. dry with materialdried with anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified with silica gel column chromatography (ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-e5ad18c8a4594a748ec3e32317f860d5
出典データセット
uspto-grants-2005_08
特許番号
US06936602B1

反応ノート

読み込み中…