Potassium Carbonate → HCID 67114429, compound

HRID 2284312Notes

Reaction equation

HRID 2284312 reaction equation
C(=O)([O-])[O-].[K+].[K+].Br[C:8]1[C:16]2[C:11](=[CH:12][C:13]([NH2:17])=[CH:14][CH:15]=2)[N:10]([S:18]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)(=[O:20])=[O:19])[CH:9]=1.[N+:27]([C:30]1[CH:35]=[CH:34][C:33](B(O)O)=[CH:32][CH:31]=1)([O-:29])=[O:28]>O1CCCC1.C(=O)(O)[O-].[Na+].C(OCC)(=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd]>[N+:27]([C:30]1[CH:35]=[CH:34][C:33]([C:8]2[C:16]3[C:11](=[CH:12][C:13]([NH2:17])=[CH:14][CH:15]=3)[N:10]([S:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)(=[O:20])=[O:19])[CH:9]=2)=[CH:32][CH:31]=1)([O-:29])=[O:28]

Participants

8

Reactant 3

HCID 11430Potassium CarbonateHCID 27735524-Nitrophenylboronic acidHCID 67113184HCID 67113184, compound

Product 1

HCID 67114429HCID 67114429, compoundYield 65.1%

Reagents, catalysts & solvents 4

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
130 °C

Procedure

A 1.0 M aqueous potassium carbonate solution (9.96 mL, 9.96 mmol) was added to a mixture of 3-bromo-1-(phenylsulfonyl)-1H-indol-6-amine (1.00 g, 2.84 mmol), (4-nitrophenyl)boronic acid (1.19 g, 7.12 mmol) and palladium tetrakis(triphenylphosphine) (164 mg, 0.14 mmol) in tetrahydrofuran (13.7 mL). The biphasic mixture was heated in a microwave at 130° C. for 10 min and was then diluted with a saturated solution of sodium bicarbonate (10.0 mL) and ethyl acetate (10.0 mL). The organic layer was washed with a saturated solution of sodium bicarbonate (2×10.0 mL), and the combined aqueous layers were extracted with ethyl acetate (3×30.0 mL). The combined organic phases were dried over magnesium sulfate, filtered and concentrated. The crude residue was purified by flash chromatography (10-25-50-71% ethyl acetate/hexane) to give an orange solid for 3-(4-nitrophenyl)-1-(phenylsulfonyl)-1H-indol-6-amine (726 mg, 1.85 mmol, 65%).

Workup

  1. washThe organic layer was washed with a saturated solution of sodium bicarbonate (2×10.0 mL)
  2. extractionthe combined aqueous layers were extracted with ethyl acetate (3×30.0 mL)
  3. dry with materialThe combined organic phases were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude residue was purified by flash chromatography (10-25-50-71% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-35e0ec63f7114adf99fac780fe24954d
Source dataset
uspto-grants-2015_09
Patent number
US09144557B2

Reaction notes

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