Sodium Carbonate → methyl 3-cyclohexyl-2-(2-formylphenyl)-1-(3-methoxy-3-oxopropyl)-1H-indole-6-carboxylate

HRID 1714071Notes

Reaction equation

HRID 1714071 reaction equation
Br[C:2]1[N:3]([CH2:21][CH2:22][C:23]([O:25][CH3:26])=[O:24])[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:33]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=1B(O)O)=[O:34]>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>[CH:11]1([C:10]2[C:9]3[C:4](=[CH:5][C:6]([C:17]([O:19][CH3:20])=[O:18])=[CH:7][CH:8]=3)[N:3]([CH2:21][CH2:22][C:23]([O:25][CH3:26])=[O:24])[C:2]=2[C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][C:35]=2[CH:33]=[O:34])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 2921892-Formylphenylboronic acidHCID 68501826methyl 2-bromo-3-cyclohexyl-1-(3-methoxy-3-oxopropyl)-1H-indole-6-carboxylate

Product 1

HCID 86604971methyl 3-cyclohexyl-2-(2-formylphenyl)-1-(3-methoxy-3-oxopropyl)-1H-indole-6-carboxylateYield 40%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

To a solution of methyl 2-bromo-3-cyclohexyl-1-(3-methoxy-3-oxopropyl)-1H-indole-6-carboxylate in dioxane (0.15 M) were added Na2CO3 (6 eq, 2 M aqueous solution), 1.6 eq of (2-formylphenyl)boronic acid and 0.2 eq of bis(triphenylphosphine)-palladium(II) dichloride. The mixture was heated at reflux for 1 h. The reaction mixture was filtered and the filtrate diluted with EtOAc. The organic phase was washed with brine and dried (Na2SO4) before being filtered and concentrated in vacuo. The crude was purified by flash chromatography (Biotage cartridge Si25M, 1:9 EtOAc/PE) to afford the title compound (40%); MS (ES+) m/z 448 (M+H)+.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 1 h
  3. filtrationThe reaction mixture was filtered
  4. additionthe filtrate diluted with EtOAc
  5. washThe organic phase was washed with brine
  6. dry with materialdried (Na2SO4)
  7. filtrationbefore being filtered
  8. concentrationconcentrated in vacuo
  9. customThe crude was purified by flash chromatography (Biotage cartridge Si25M, 1:9 EtOAc/PE)

Sources & evidence

ORD record
ord-845bee40f05f47debaa01d4b461b3d88
Source dataset
uspto-grants-2010_09
Patent number
US07795247B2

Reaction notes

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