Potassium Carbonate → 6-[3-(1,3,3-Trimethyl-2-oxo-2,3-dihydro-1H-indol-6-yloxymethyl)-phenyl]-hexanoic Acid Methyl Ester

HRID 988258ノート

反応式

HRID 988258 の反応式
[OH:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH3:14])([CH3:13])[C:7](=[O:12])[N:8]2C)=[CH:4][CH:3]=1.[CH3:15][O:16][C:17](=[O:31])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([CH2:29]Br)[CH:24]=1.[C:32](=O)([O-])[O-].[K+].[K+]>CN(C=O)C.CCOC(C)=O>[CH3:15][O:16][C:17](=[O:31])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([CH:29]([O:1][C:2]2[CH:10]=[C:9]3[C:5]([C:6]([CH3:13])([CH3:14])[C:7](=[O:12])[NH:8]3)=[CH:4][CH:3]=2)[CH3:32])[CH:24]=1

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 219317776-hydroxy-1,3,3-trimethyl-2,3-dihydro-1H-indol-2-oneHCID 542191176-(3-Bromomethyl-phenyl)-hexanoic Acid Methyl Ester

生成物 1

HCID 692161446-[3-(1,3,3-Trimethyl-2-oxo-2,3-dihydro-1H-indol-6-yloxymethyl)-phenyl]-hexanoic Acid Methyl Ester収率 41.5%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
60 °C

実験手順

To a solution of 6-hydroxy-1,3,3-trimethyl-1,3-dihydro-indol-2-one (396 mg, 2.07 mmol) in DMF (7.6 mL) is added 6-(3-Bromomethyl-phenyl)-hexanoic acid methyl ester (682 mg, 2.28 mmol) and potassium carbonate (315 mg, 2.28 mmol). The resulting mixture is heated to 60° C., stirred for 2 hrs. then cooled to room temp and diluted with EtOAc. The organic layer is washed with water, brine, dried over MgSO4 and concentrated. The residue is purified by flash chromatography (eluting with 30% ethyl acetate/hexanes) to give 352 mg of title compound. MS (ESI) 410 (M+H)+.

後処理

  1. temperaturethen cooled to room temp
  2. washThe organic layer is washed with water, brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customThe residue is purified by flash chromatography (eluting with 30% ethyl acetate/hexanes)

出典と根拠

ORDレコード
ord-41a6895f53ba4afea93c2989834d5a19
出典データセット
uspto-grants-2003_10
特許番号
US06635655B1

反応ノート

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