Potassium Carbonate → {2-[3-cyclohexyl-6-(methoxycarbonyl)-1-methyl-1H-indol-2-yl]phenoxy}acetic acid

HRID 1807632ノート

反応式

HRID 1807632 の反応式
[CH:1]1([C:7]2[C:15]3[C:10](=[CH:11][C:12]([C:16]([O:18][CH3:19])=[O:17])=[CH:13][CH:14]=3)[N:9]([CH3:20])[C:8]=2[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[OH:27])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Br[CH2:29][C:30]([O:32]CCCC)=[O:31].C(=O)([O-])[O-].[K+].[K+]>>[CH:1]1([C:7]2[C:15]3[C:10](=[CH:11][C:12]([C:16]([O:18][CH3:19])=[O:17])=[CH:13][CH:14]=3)[N:9]([CH3:20])[C:8]=2[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[O:27][CH2:29][C:30]([OH:32])=[O:31])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

参加物

4

反応物 3

HCID 11430Potassium CarbonateHCID 87883Butyl bromoacetateHCID 58317807methyl 3-cyclohexyl-2-(2-hydroxyphenyl)-1-methyl-1H-indole-6-carboxylate

生成物 1

HCID 58317804{2-[3-cyclohexyl-6-(methoxycarbonyl)-1-methyl-1H-indol-2-yl]phenoxy}acetic acid収率 90.6%

実験手順

A solution of intermediate 4 (4.00 g, 11.0 mmol), tent-butyl 2-bromoacetate (2.36 g, 12.1 mmol) and potassium carbonate (3.04 g, 22.0 mmol) was stirred at room temperature. After 72 h, the reaction mixture was concentrated under vacuum and the residue was partitioned between CH2Cl2 and water. The organic layer was dried and the residue was reconstituted in CH2Cl2 (20 mL) and TFA (20 mL) was added. After 2 h at room temperature, the reaction mixture was evaporated under vacuum to yield 4.2 g (90%) of {2-[3-cyclohexyl-6-(methoxycarbonyl)-1-methyl-1H-indol-2-yl]phenoxy}acetic acid 5: m/z=422 (M+H)+.

後処理

  1. concentrationthe reaction mixture was concentrated under vacuum
  2. customthe residue was partitioned between CH2Cl2 and water
  3. customThe organic layer was dried
  4. additionTFA (20 mL) was added
  5. waitAfter 2 h at room temperature
  6. customthe reaction mixture was evaporated under vacuum

出典と根拠

ORDレコード
ord-03270805739849bea63906bf04f32bb0
出典データセット
uspto-grants-2013_01
特許番号
US08357687B2

反応ノート

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