Potassium Carbonate → tert-butyl 3-cyclohexyl-2-[2-(2-methoxy-2-oxoethoxy)phenyl]-1-methyl-1H-indole-6-carboxylate

HRID 1807640Notes

Reaction equation

HRID 1807640 reaction equation
[CH:1]1([C:7]2[C:15]3[C:10](=[CH:11][C:12]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=[CH:13][CH:14]=3)[N:9]([CH3:23])[C:8]=2[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[OH:30])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Br[CH2:32][C:33]([O:35][CH3:36])=[O:34].C(=O)([O-])[O-].[K+].[K+]>CC#N>[CH:1]1([C:7]2[C:15]3[C:10](=[CH:11][C:12]([C:16]([O:18][C:19]([CH3:22])([CH3:20])[CH3:21])=[O:17])=[CH:13][CH:14]=3)[N:9]([CH3:23])[C:8]=2[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[O:30][CH2:32][C:33]([O:35][CH3:36])=[O:34])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 58317805tert-butyl 3-cyclohexyl-2-(2-hydroxyphenyl)-1-methyl-1H-indole-6-carboxylate

Product 1

HCID 58317834tert-butyl 3-cyclohexyl-2-[2-(2-methoxy-2-oxoethoxy)phenyl]-1-methyl-1H-indole-6-carboxylateYield 97.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of intermediate 25 (0.6 g, 1.5 mmol), methyl 2-bromoacetate (0.281 g, 1.83 mmol) and potassium carbonate (0.423 g, 3.06 mmol) in MeCN 50 mL was stirred at room temperature. After 12 h, the reaction mixture was concentrated under vacuum and the residue was partitioned between CH2Cl2 and water. The organic layer was dried and evaporated under vacuum to yield 0.7 g (96%) of tert-butyl 3-cyclohexyl-2-[2-(2-methoxy-2-oxoethoxy)phenyl]-1-methyl-1H-indole-6-carboxylate 26: m/z=478 (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. customevaporated under vacuum

Sources & evidence

ORD record
ord-bfb00a8569d94b2d872d04b2b684df26
Source dataset
uspto-grants-2013_01
Patent number
US08357687B2

Reaction notes

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