Sodium Carbonate → HCID 67346622, compound

HRID 1669491Notes

Reaction equation

HRID 1669491 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.N1C2C(=CC=C(C(OC)=O)C=2)C=C1.[CH3:34][O:35][C:36]1[CH:41]=[CH:40][C:39](B2OC(C)(C)C(C)(C)O2)=[C:38]([O:51][CH2:52][O:53][CH3:54])[CH:37]=1.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.CCOC(C)=O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[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:39]2[CH:40]=[CH:41][C:36]([O:35][CH3:34])=[CH:37][C:38]=2[O:51][CH2:52][O:53][CH3:54])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 639844Methyl indole-6-carboxylateHCID 11175076Methyl 2-bromo-3-cyclohexyl-1H-indole-6-carboxylateHCID 46854347HCID 46854347, compound

Product 1

HCID 67346622HCID 67346622, compoundYield 93%

Reagents, catalysts & solvents 3

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of methyl 2-bromo-3-cyclohexyl-1H-indole-6-carboxylate (prepared as described in International patent application WO2004087714, from commercially available methyl indole-6-carboxylate), 2-[4-methoxy-2-(methoxymethoxy)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (2 eq) and 2 M Na2CO3 (aq) (6 eq) in dioxane (0.15 M) was prepared. Then the mixture was degassed with nitrogen and bis(triphenylphosphine)palladium (II) chloride (0.2 eq) was added. The resulting mixture was immersed in a pre-heated oil bath at 110° C. for 2 h. The mixture was cooled, diluted with EtOAc, washed with 1 N HCl (aq), brine, dried (Na2SO4), filtered and the solvent removed in vacuo. The crude was purified by automated FC (PE/EtOAc 9:1) to afford the product (93%). (ES+) m/z 424 (M+H)+.

Workup

  1. customprepared
  2. customwas prepared
  3. additionwas added
  4. temperatureThe mixture was cooled
  5. washwashed with 1 N HCl (aq), brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. customthe solvent removed in vacuo
  9. customThe crude was purified by automated FC (PE/EtOAc 9:1)

Sources & evidence

ORD record
ord-d2046db20a1b415695320f7299a55994
Source dataset
uspto-grants-2011_08
Patent number
US07989438B2

Reaction notes

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