Potassium Carbonate → 5-(3-Chloro-phenyl)-3,3-dimethyl-1,3-dihydro-indol-2-one

HRID 9321Notes

Reaction equation

HRID 9321 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2([CH3:13])[CH3:12].[Cl:14][C:15]1[CH:16]=[C:17](B(O)O)[CH:18]=[CH:19][CH:20]=1.C(=O)([O-])[O-].[K+].[K+]>C(COC)OC.O.[Cl-].[NH4+].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:14][C:15]1[CH:20]=[C:19]([C:2]2[CH:3]=[C:4]3[C:8](=[CH:9][CH:10]=2)[NH:7][C:6](=[O:11])[C:5]3([CH3:13])[CH3:12])[CH:18]=[CH:17][CH:16]=1

Participants

8

Reactant 3

HCID 11430Potassium CarbonateHCID 2734323(3-Chlorophenyl)boronic acidHCID 120527965-bromo-3,3-dimethyl-2,3-dihydro-1H-indol-2-one

Product 1

HCID 98169215-(3-Chloro-phenyl)-3,3-dimethyl-1,3-dihydro-indol-2-oneYield 25%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolventHCID 25517Ammonium ChlorideSolvent

Procedure

5-bromo-1,3-dihydro-3,3-dimethyl-2H-indol-2-one (0.98 g, 4.07 mol) and tetrakis(triphenylphosphine)palladium(0) (0.239 g) were stirred under an atmosphere of nitrogen in dimethoxyethane (35 cm3). After 15 min., 3-chlorophenylboronic acid (1.27 g, 8.13 mol) was added, followed by potassium carbonate (3.40 g, 45 mmol) in water (15 cm3). The reaction was heated to reflux for 2 hours and then stirred at room temperature overnight. The mixture was diluted with sat. ammonium chloride and extracted with EtOAc (×3). The combined organic layers were dried (MgSO4), filtered, and evaporated. The residue was purified by column chromatography (SiO2, EtOAc:hexane, 1:3) to afford the subtitled compound (0.284 g, 25%): mp 188–189° C.; 1H NMR (DMSO-d6) δ 3.34 (s, 6 H), 6.93 (d, 1 H, J=8.04 Hz), 7.38–7.35 (m, 1 H), 7.53–7.43 (m, 2 H), 7.61 (d, 1 H, J=7.68 Hz), 7.70 (s, 2 H), 10.40 (s, 1 H); IR (KBr) 3420, 3150, 3050, 1700 cm−1; MS (EI) m/z 270 (M−H)−; CHN calculated for C16H14ClNO+0.1 C4H8O2: C, 70.21; H, 5.32; N, 4.99. Found: C, 70.3; H, 5.44; N, 4.93.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 2 hours
  3. extractionextracted with EtOAc (×3)
  4. dry with materialThe combined organic layers were dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by column chromatography (SiO2, EtOAc:hexane, 1:3)

Sources & evidence

ORD record
ord-b9142de5693444da9440ade37d4c5c15
Source dataset
uspto-grants-2006_08
Patent number
US07091234B2

Reaction notes

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