Tricyclohexylphosphine → HCID 86590248, compound

HRID 2212608Notes

Reaction equation

HRID 2212608 reaction equation
Br[C:2]1[CH:7]=[C:6]([CH3:8])[C:5](OC)=[CH:4][C:3]=1[N:11]([CH2:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=1)[C:12](=[O:16])[CH:13]([CH3:15])[CH3:14].CC(C)([O-])C.[Na+].C1(P(C2CCCCC2)C2CCCCC2)CCCCC1>O1CCOCC1.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:25][O:24][C:21]1[CH:22]=[CH:23][C:18]([CH2:17][N:11]2[C:3]3[C:2](=[CH:7][C:6]([CH3:8])=[CH:5][CH:4]=3)[C:13]([CH3:14])([CH3:15])[C:12]2=[O:16])=[CH:19][CH:20]=1

Participants

7

Reactant 3

HCID 75806TricyclohexylphosphineHCID 21966461HCID 21966461, compoundHCID 23676156Sodium t-butoxide

Product 1

HCID 86590248HCID 86590248, compoundYield 77%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of N-(2-bromo-5-methoxy-4-methyl-phenyl)-N-(4-methoxy-benzyl)-isobutyramide (8.72 g, 21.4 mmol) in dry 1,4-dioxane (80 mL) was added sodium tert-butoxide (3.09 g, 32.1 mmol). Argon was bubbled through for about 15 minutes before adding palladium(II) acetate (241 mg, 1.07 mmol) and tricyclohexylphosphine (300 mg, 1.07 mmol). The mixture was heated to reflux for 16 hours. The mixture was cooled to room temperature, diluted with water and extracted with EtOAc, washed with brine, dried over MgSO4, filtered and evaporated. The residue was purified by column chromatography on silica gel (hexane: EtOAc/5:1 to 3:1) to give 5.4 g of 6-Methoxy-1-(4-methoxy-benzyl-3,3,5-trimethyl-1,3-dihydro-indol-2-one (77%). 1H NMR (300 MHz, CDCl3, ppm): δ: 1.38 (s, 6 H), 2.16(s, 3 H), 3.71(s, 3 H), 3.77 (s, 3 H), 4.84 (s, 2 H), 6.28 (s, 1 H), 6.82–6.85(m, 2 H), 6.95(s, 1 H), 7.19–7.22 (m, 2 H).

Workup

  1. customArgon was bubbled through for about 15 minutes
  2. temperatureThe mixture was heated
  3. temperatureto reflux for 16 hours
  4. extractionextracted with EtOAc
  5. washwashed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was purified by column chromatography on silica gel (hexane: EtOAc/5:1 to 3:1)

Sources & evidence

ORD record
ord-67cf6299e77b4aa2bbaa2c747d3acc0d
Source dataset
uspto-grants-2006_09
Patent number
US07102000B2

Reaction notes

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