Water → isopropyl-methyl-carbamic acid 4-(3-cyano-1-ethyl-6-methoxy-1H-indol-2-yl)-phenyl ester

HRID 502246ノート

反応式

HRID 502246 の反応式
[CH2:1]([N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[C:5]([C:14]#[N:15])=[C:4]1C1C=CC(O)=CC=1)[CH3:2].Cl[C:24]([O:26][C:27]1[CH:32]=[CH:31][C:30]([N+]([O-])=O)=[CH:29][CH:28]=1)=[O:25].[CH:36]([NH:39][CH3:40])([CH3:38])[CH3:37].O>CCN(CC)CC.C(Cl)Cl.C(OCC)(=O)C>[C:14]([C:5]1[C:6]2[C:11](=[CH:10][C:9]([O:12][CH3:13])=[CH:8][CH:7]=2)[N:3]([CH2:1][CH3:2])[C:4]=1[C:30]1[CH:31]=[CH:32][C:27]([O:26][C:24](=[O:25])[N:39]([CH:36]([CH3:38])[CH3:37])[CH3:40])=[CH:28][CH:29]=1)#[N:15]

参加物

8

反応物 4

HCID 962WaterHCID 78485N-MethylisopropylamineHCID 821294-Nitrophenyl chloroformateHCID 594253351-ethyl-2-(4-hydroxyphenyl)-6-methoxy-1H-indole-3-carbonitrile

生成物 1

HCID 59425594isopropyl-methyl-carbamic acid 4-(3-cyano-1-ethyl-6-methoxy-1H-indol-2-yl)-phenyl ester収率 70%

試薬・触媒・溶媒 3

HCID 6344Dichloromethane溶媒HCID 8471Triethylamine溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of 1-ethyl-2-(4-hydroxyphenyl)-6-methoxy-1H-indole-3-carbonitrile (58 mg, 0.2 mmol) in 4 mL of Et3N and CH2Cl2 (1/1) is added p-nitrophenyl chloroformate (100 mg, 0.5 mmol) at room temperature. After the mixture is stirred for about 1 h, N-isopropylmethylamine (0.062 mL, 0.6 mmol) is added. The mixture is stirred for 3 h and then water and ethyl acetate are added to the reaction mixture. The organic layer is separated, washed with aqueous HCl (1N) and brine, dried over anhydrous Na2SO4, and filtered and concentrated. The crude solid is purified by preparative HPLC to afford 70% of isopropyl-methyl-carbamic acid 4-(3-cyano-1-ethyl-6-methoxy-1H-indol-2-yl)-phenyl ester.

後処理

  1. stirringThe mixture is stirred for 3 h
  2. customThe organic layer is separated
  3. washwashed with aqueous HCl (1N) and brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude solid is purified by preparative HPLC

出典と根拠

ORDレコード
ord-7427fe0c2a6f404ab1afc8a7ad10eba2
出典データセット
uspto-grants-2010_08
特許番号
US07772271B2

反応ノート

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