Sodium Carbonate → HCID 86761176, compound

HRID 1714066

Reaction equation

HRID 1714066 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:41]=[CH:40][O:39][C:38]=1B(O)O)=[O:36].B(O)O>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[O:39][CH:40]=[CH:41][C:37]=1[CH:35]=[O:36])([CH3:28])([CH3:27])[CH3:26]

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 61668Boronic Acid2×HCID 37393373-Formylfuran-2-boronic acidHCID 29943315HCID 29943315, compound

Product 1

HCID 86761176HCID 86761176, compoundYield 38%

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 (prepared as described in Example 1, Step 1) in dioxane (0.04 M) was added Na2CO3 (5 eq, 2 M aqueous solution), 3-formylfuran-2-boronic acid (1.4 eq) and bis(triphenylphosphine)palladium(II) dichloride (0.2 eq). The mixture was heated at reflux for 20 mins, at which point the heat was removed and the reaction cooled slightly to allow addition of a further 1 eq of boronic acid. The reaction was then heated for a further 1 h at reflux. Again, the reaction was cooled slightly to allow addition of a further 0.5 eq of boronic acid. After heating for a further 30 mins, the reaction was allowed to cool to RT, filtered and the filtrate diluted with EtOAc. The organic phase was washed with H2O and dried (Na2SO4) before being filtered and concentrated in vacuo. The crude was purified by flash chromatography (10-20% EtOAc/PE) to afford the title compound as an oil (38%); MS (ES+) m/z 466 (M+H)+, 488 (M+Na)+.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 20 mins, at which
  3. customwas removed
  4. temperaturethe reaction cooled slightly
  5. temperatureThe reaction was then heated for a further 1 h
  6. temperatureat reflux
  7. temperatureAgain, the reaction was cooled slightly
  8. temperatureAfter heating for a further 30 mins
  9. filtrationfiltered
  10. additionthe filtrate diluted with EtOAc
  11. washThe organic phase was washed with H2O
  12. dry with materialdried (Na2SO4)
  13. filtrationbefore being filtered
  14. concentrationconcentrated in vacuo
  15. customThe crude was purified by flash chromatography (10-20% EtOAc/PE)

Sources & evidence

ORD record
ord-56213daeba644e7695ed53485c57370d
Source dataset
uspto-grants-2010_09
Patent number
US07795247B2

Linked notes

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