Benzyl Alcohol → Phenylmethyl 2,3-dihydro-1-methyl-2-oxo-1H-indole-5-carboxylate

HRID 1976780Notes

Reaction equation

HRID 1976780 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH3:11])[C:6](=[O:12])[CH2:5]2.C(N(CC)CC)C.[CH2:20]([OH:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C1C[O:31][CH2:30]C1>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]>[CH3:11][N:7]1[C:8]2[C:4](=[CH:3][C:2]([C:30]([O:27][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[O:31])=[CH:10][CH:9]=2)[CH2:5][C:6]1=[O:12]

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 24326665-Bromo-1-methyl-2-oxoindoline

Product 1

HCID 21998744Phenylmethyl 2,3-dihydro-1-methyl-2-oxo-1H-indole-5-carboxylate

Reagents, catalysts & solvents 1

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)Catalyst

Conditions

Temperature
130 °C

Procedure

A solution of 5-bromo-1-methyl oxindole (3.75 g, 16.6 mmol) and triethylamine (3.48 mL) in THF (40 mL) was treated with benzyl alcohol (2.58 mL) and PdCl2(dppf) (300 mg), stirred under carbon monoxide (680 psi) at 130° C. for 16 hours, depressurized, filtered through diatomaceous earth (Celite®), and concentrated. The concentrate was purified on silica gel with 30% ethyl acetate/hexanes to provide 2.36 g of the desired product.

Workup

  1. filtrationfiltered through diatomaceous earth (Celite®)
  2. concentrationconcentrated
  3. customThe concentrate was purified on silica gel with 30% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-e1162bedb14248e2ae3d2451e161fd4e
Source dataset
uspto-grants-2001_05
Patent number
US06228868B1

Reaction notes

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