Chloride → HCID 86627895, compound

HRID 1669412Notes

Reaction equation

HRID 1669412 reaction equation
Br[C:2]1[NH:3][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.[CH3:21][O:22][CH2:23][O:24][C:25]1[CH:30]=[C:29]([O:31][S:32]([C:35]2[CH:40]=[CH:39][C:38]([CH3:41])=[CH:37][CH:36]=2)(=[O:34])=[O:33])[CH:28]=[CH:27][C:26]=1B(O)O.[Cl-].C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1>[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)[NH:3][C:2]=2[C:26]2[CH:27]=[CH:28][C:29]([O:31][S:32]([C:35]3[CH:40]=[CH:39][C:38]([CH3:41])=[CH:37][CH:36]=3)(=[O:34])=[O:33])=[CH:30][C:25]=2[O:24][CH2:23][O:22][CH3:21])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

6

Reactant 4

HCID 312ChlorideHCID 10340Sodium CarbonateHCID 11175076Methyl 2-bromo-3-cyclohexyl-1H-indole-6-carboxylateHCID 86627894HCID 86627894, compound

Product 1

HCID 86627895HCID 86627895, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

Methyl 2-bromo-3-cyclohexyl-1H-indole-6-carboxylate (prepared as in International patent application WO 2004/087714), (2-(methoxymethoxy)-4-{[(4-methylphenyl)-sulfonyl]oxy}phenyl)boronic acid (1 eq) and bis(triphenylphosphinepalladium(II) chloride (0.1 eq) were dissolved in dioxane (0.08M). The solution was degassed and flushed with argon. A 2M aqueous solution of Na2CO3 (1 eq) was added and the mixture was heated to 100° C. After 3 h the temperature was raised to 110° C. Heating was continued overnight. All volatiles were evaporated and the residual material was dissolved in EtOAc. The solution was washed with 1N aqueous HCl, sat. aq. NaHCO3 and brine. After drying over Na2SO4 all volatiles were evaporated in vacuo. The residual material was subjected to FC (PE:EtOAc, 8:2). After evaporation of the product fractions the product was obtained as a light orange amorphous solid (58%). (ES+) m/z 564 (M+H)+.

Workup

  1. customThe solution was degassed
  2. customflushed with argon
  3. temperatureAfter 3 h the temperature was raised to 110° C
  4. temperatureHeating
  5. customAll volatiles were evaporated
  6. dissolutionthe residual material was dissolved in EtOAc
  7. washThe solution was washed with 1N aqueous HCl, sat. aq. NaHCO3 and brine
  8. dry with materialAfter drying over Na2SO4 all volatiles
  9. customwere evaporated in vacuo
  10. customAfter evaporation of the product fractions the product

Sources & evidence

ORD record
ord-360e9104117e4ca9b2dcc8d9767fac58
Source dataset
uspto-grants-2011_08
Patent number
US07989438B2

Reaction notes

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