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

HRID 1807632Notes

Reaction equation

HRID 1807632 reaction equation
[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

Participants

4

Reactant 3

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

Product 1

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

Procedure

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)+.

Workup

  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

Sources & evidence

ORD record
ord-03270805739849bea63906bf04f32bb0
Source dataset
uspto-grants-2013_01
Patent number
US08357687B2

Reaction notes

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