Sodium Carbonate → methyl 1-(2-tert-butoxy-2-oxoethyl)-3-cyclohexyl-2-(2-formylphenyl)-1H-indole-6-carboxylate

HRID 1713987Notes

Reaction equation

HRID 1713987 reaction equation
Br[C:2]1[N:3]([CH2:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[C:4]2[C:9]([C:10]=1[CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)=[CH:8][CH:7]=[C:6]([C:17]([O:19][CH3:20])=[O:18])[CH:5]=2.C([O-])([O-])=O.[Na+].[Na+].[CH:35]([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=1B(O)O)=[O:36]>O1CCOCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:25]([O:24][C:22](=[O:23])[CH2:21][N:3]1[C:4]2[C:9](=[CH:8][CH:7]=[C:6]([C:17]([O:19][CH3:20])=[O:18])[CH:5]=2)[C:10]([CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)=[C:2]1[C:38]1[CH:39]=[CH:40][CH:41]=[CH:42][C:37]=1[CH:35]=[O:36])([CH3:28])([CH3:27])[CH3:26]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 2921892-Formylphenylboronic acidHCID 299433152-Bromo-1-tert-butoxycarbonylmethyl-3-cyclohexyl-1H-indole-6-carboxylic acid methyl ester

Product 1

HCID 86604961methyl 1-(2-tert-butoxy-2-oxoethyl)-3-cyclohexyl-2-(2-formylphenyl)-1H-indole-6-carboxylateYield 53%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

To a solution of methyl 2-bromo-1-(2-tert-butoxy-2-oxoethyl)-3-cyclohexyl-1H-indole-6-carboxylate in 1,4-dioxane (0.15 M) was added Na2CO3 (6 eq, 2 M solution), (2-formylphenyl)boronic acid (1.5 eq) and bis(triphenylphosphine)palladium(II) dichloride (0.2 eq) and the mixture heated at reflux for 45 min. The reaction mixture was allowed to cool and filtered. The filtrate was diluted with EtOAc and the organic phase washed with H2O, brine and dried over Na2SO4 before being filtered and concentrated in vacuo. The crude material was purified by flash chromatography (1:9 EtOAc/PE) to afford the title compound as a yellow solid (53%); MS (ES+) m/z 476 (M+H)+

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for 45 min
  3. temperatureto cool
  4. filtrationfiltered
  5. additionThe filtrate was diluted with EtOAc
  6. washthe organic phase washed with H2O, brine
  7. dry with materialdried over Na2SO4
  8. filtrationbefore being filtered
  9. concentrationconcentrated in vacuo
  10. customThe crude material was purified by flash chromatography (1:9 EtOAc/PE)

Sources & evidence

ORD record
ord-30d686cbfdcb4169ab89fa1d399eb0bb
Source dataset
uspto-grants-2010_09
Patent number
US07795247B2

Reaction notes

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