Potassium Carbonate → HCID 50991548, compound

HRID 2192256Notes

Reaction equation

HRID 2192256 reaction equation
CN(C=O)C.O.Br[C:8]1[C:16]2[C:11](=[CH:12][C:13]([N:17]3[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH2:18]3)=[CH:14][CH:15]=2)[N:10]([C:30]2[CH:35]=[CH:34][N:33]=[CH:32][CH:31]=2)[CH:9]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:42][O:43][C:44]1[CH:49]=[CH:48][C:47](B(O)O)=[CH:46][CH:45]=1>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].O.C(OCC)(=O)C>[CH3:42][O:43][C:44]1[CH:49]=[CH:48][C:47]([C:8]2[C:16]3[C:11](=[CH:12][C:13]([N:17]4[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH2:18]4)=[CH:14][CH:15]=3)[N:10]([C:30]3[CH:35]=[CH:34][N:33]=[CH:32][CH:31]=3)[CH:9]=2)=[CH:46][CH:45]=1

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 201262(4-Methoxyphenyl)boronic acidHCID 21962138N,N-Dimethylformamide--water (1/1)HCID 50991462tert-butyl 4-(3-bromo-1-(pyridin-4-yl)-1H-indol-6-yl)piperazine-1-carboxylate

Product 1

HCID 50991548HCID 50991548, compoundYield 100.6%

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

DMF/water (4:1, 2 mL) was added to a mixture of tert-butyl 4-(3-bromo-1-(pyridin-4-yl)-1H-indol-6-yl)piperazine-1-carboxylate (29 mg, 0.0636 mmol), potassium carbonate (18 mg, 0.13 mmol) and 4-methoxyphenylboronic acid (11 mg, 0.070 mmol) and the dissolved gas was removed. After adding Pd(dppf)Cl2 (10.4 mg, 0.013 mmol), the mixture was stirred at room temperature for 14 hours. After adding ethyl acetate and water, the mixture was filtered using a diatomite pad. After separation of the organic layer, the aqueous layer was extracted with ethyl acetate. The collected organic layer was washed with brine and concentrated under reduced pressure by drying with anhydrous magnesium sulfate. The residue was purified by chromatography (silica gel, EA:Hx=1:4 1:1). The target compound (31 mg) was obtained as white solid.

Workup

  1. customthe dissolved gas was removed
  2. filtrationthe mixture was filtered
  3. customAfter separation of the organic layer
  4. extractionthe aqueous layer was extracted with ethyl acetate
  5. washThe collected organic layer was washed with brine
  6. concentrationconcentrated under reduced pressure
  7. dry with materialby drying with anhydrous magnesium sulfate
  8. customThe residue was purified by chromatography (silica gel, EA:Hx=1:4 1:1)

Sources & evidence

ORD record
ord-feab49c19042444fbb53b085cb6a88d3
Source dataset
uspto-grants-2012_12
Patent number
US08329708B2

Reaction notes

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