Potassium Carbonate → 2-Methyl-5-(1-methyl-piperidin-3-ylmethoxy)-1H-indole-3-carboxylic Acid Benzyl Ester

HRID 966506

反応式

HRID 966506 の反応式
[CH3:1][N:2]1[CH2:7][CH2:6][CH2:5][CH:4]([CH2:8][O:9]S(C2C=CC(C)=CC=2)(=O)=O)[CH2:3]1.[CH3:20][C:21]1[NH:22][C:23]2[C:28]([C:29]=1[C:30]([O:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[O:31])=[CH:27][C:26](O)=[CH:25][CH:24]=2.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C.CO.C(N(CC)CC)C>C(#N)C>[CH2:33]([O:32][C:30]([C:29]1[C:28]2[C:23](=[CH:24][CH:25]=[C:26]([O:9][CH2:8][CH:4]3[CH2:5][CH2:6][CH2:7][N:2]([CH3:1])[CH2:3]3)[CH:27]=2)[NH:22][C:21]=1[CH3:20])=[O:31])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

参加物

6

反応物 4

HCID 11430Potassium CarbonateHCID 109239755-Hydroxy-2-methyl-1H-indole-3-carboxylic acid benzyl esterHCID 21184160Toluene-4-sulfonic acid 1-methyl-piperidin-3-ylmethyl esterHCID 21980445Ethyl acetate methanol triethylamine

生成物 1

HCID 101786242-Methyl-5-(1-methyl-piperidin-3-ylmethoxy)-1H-indole-3-carboxylic Acid Benzyl Ester収率 24%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

Toluene-4-sulfonic acid 1-methyl-piperidin-3-ylmethyl ester (0.753 g, 2.66 mmol, 1.0 eq) was dissolved in dry acetonitrile (30 mL), and treated with 2-methyl-3-benzyloxycarbonyl-5-hydroxyindole (0.759 g, 2.70 mmol, 1 eq) and potassium carbonate (0.690 g, 5 mmol, 2.0 eq.). The reaction was heated to reflux and followed by TLC (ethyl acetate/methanol/triethylamine 87/10/3). After 96 hours, the reaction was loaded directly on silica gel and chromatographed (ethyl acetate/methanol/triethylamine 87/10/3) to afford a white solid: 0.237 g (24% yield). This was converted to the corresponding hydrochloride salt: LC/MS (ESI+) 393 (M+1), Anal. (C24H28N2O3.HCl.0.6H2O) C, H, N.

後処理

  1. temperatureThe reaction was heated
  2. temperatureto reflux
  3. customchromatographed (ethyl acetate/methanol/triethylamine 87/10/3)
  4. customto afford a white solid

出典と根拠

ORDレコード
ord-64dce8e451494a51a848ab87e53b3f05
出典データセット
uspto-grants-2005_10
特許番号
US06951848B2

関連ノート

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