Potassium Carbonate → HCID 86698607, compound

HRID 1054604Notes

Reaction equation

HRID 1054604 reaction equation
CC1(C)COB([C:8]2[CH:13]=[CH:12][C:11]([CH:14]3[CH2:18][CH2:17][N:16]([C:19](=[O:21])[CH3:20])[CH2:15]3)=[CH:10][CH:9]=2)OC1.Br[C:24]1[CH:25]=[C:26]2[C:30](=[CH:31][C:32]=1[Cl:33])[NH:29][CH:28]=[C:27]2[CH:34]=[O:35].C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.C(O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[C:19]([N:16]1[CH2:17][CH2:18][CH:14]([C:11]2[CH:10]=[CH:9][C:8]([C:24]3[CH:25]=[C:26]4[C:30](=[CH:31][C:32]=3[Cl:33])[NH:29][CH:28]=[C:27]4[CH:34]=[O:35])=[CH:13][CH:12]=2)[CH2:15]1)(=[O:21])[CH3:20]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 866985665-bromo-6-chloro-1H-indole-3-carbaldehydeHCID 86698606HCID 86698606, compound

Product 1

HCID 86698607HCID 86698607, compoundYield 37.3%

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

To a degassed mixture of crude 1-{3-[4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)phenyl]pyrrolidin-1-yl}ethanone (assume 0.38 mmol), 5-bromo-6-chloro-1H-indole-3-carbaldehyde (98.4 mg, 0.38 mmol) and 2 N aqueous potassium carbonate (0.76 mL, 1.52 mmol) in toluene (2.25 mL) and ethanol (0.75 mL) was added [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (27.8 mg, 0.038 mmol). The reaction mixture was heated to 110° C. in a microwave for 30 minutes. After cooling to room temperature, the reaction mixture was partitioned between water and EtOAc. The organic phase was washed with brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified by flash column (first EtOAc in Petroleum ether, then MeOH in CH2Cl2) to give 5-[4-(1-acetylpyrrolidin-3-yl)phenyl]-6-chloro-1H-indole-3-carbaldehyde (52 mg) as an orange solid. MS (ES+) 389.0 (M+Na)+

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe reaction mixture was partitioned between water and EtOAc
  3. washThe organic phase was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash column (first EtOAc in Petroleum ether

Sources & evidence

ORD record
ord-f46dc6c64aaf445ea7e07996c7051169
Source dataset
uspto-grants-2016_07
Patent number
US09394285B2

Reaction notes

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