Water → 6-Pyridin-3-yl-1,3-dihydro-indol-2-one

HRID 1615205Notes

Reaction equation

HRID 1615205 reaction equation
Cl[C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1.CC1(C)C(C)(C)CB([C:20]2[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=2)C1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].O>CCCCO.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1>[N:22]1[CH:23]=[CH:24][CH:25]=[C:20]([C:2]2[CH:10]=[C:9]3[C:5]([CH2:6][C:7](=[O:11])[NH:8]3)=[CH:4][CH:3]=2)[CH:21]=1

Participants

8

Reactant 4

HCID 962WaterHCID 62657Potassium Phosphate, TribasicHCID 7363446-Chloro-1,3-dihydroindol-2-oneHCID 68733397HCID 68733397, compound

Product 1

HCID 219155796-Pyridin-3-yl-1,3-dihydro-indol-2-oneYield 80%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylCatalystHCID 2631-ButanolSolvent

Conditions

Temperature
100 °C

Procedure

A mixture 6-chloroindolin-2-one (100 mg, 0.60 mmol), 3-(3,3,4,4-tetramethylborolan-1-yl)pyridine (184 mg, 0.90 mmol), Pd2dba3 (5.4 mg, 0.0060 mmol) and powdered K3PO4 (252 mg, 1.2 mmol) in n-BuOH (2 mL) was degassed by evacuation and refilling with Ar. Dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine (11.4 mg, 0.024 mmol) was added under the atmosphere of Ar. The reaction mixture was sealed and heated with stirring under microwave irradiation at 100° C. for 99 min. Later the reaction was cooled to rt and treated with degassed H2O (0.25 mL). The mixture was reheated under microwave irradiation at 110° C. for 1 h. The crude reaction mixture was concentrated under reduced pressure and purified by flash chromatography on silica gel using MeOH (0 to 6%) in DCM as the eluent to provide the title compound as a pale yellow solid (100 mg, 80%). %). 1H NMR (400 MHz, CD3OD) δ ppm 8.77 (d, J=1.52 Hz, 1H), 8.52 (dd, J4.80, 1.52 Hz, 1H), 8.05-8.10 (m, 1H), 7.52 (dd, J7.33, 4.80 Hz, 1H), 7.39 (d, J=7.6 Hz, 1H), 7.30 (dd, J=7.71, 1.39 Hz, 1H), 7.17 (s, 1H), 3.59 (s, 2H); MS ESI 211.0 (100) [M+H]+, calcd for [C13H10N2O+H]+ 211.2.

Workup

  1. customThe reaction mixture was sealed
  2. temperatureheated
  3. temperatureLater the reaction was cooled to rt
  4. customThe mixture was reheated under microwave irradiation at 110° C. for 1 h
  5. customThe crude reaction mixture
  6. concentrationwas concentrated under reduced pressure
  7. custompurified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-8674d9fb63304147abd01386c4bc0fdf
Source dataset
uspto-grants-2014_07
Patent number
US08765748B2

Reaction notes

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