Methanol → Methyl 1-(4-methoxybutyl)-3,3-dimethyl-2-oxoindoline-6-carboxylate

HRID 1942537Notes

Reaction equation

Br[C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH3:19])([CH3:18])[C:7](=[O:17])[N:8]2[CH2:11][CH2:12][CH2:13][CH2:14][O:15][CH3:16])=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C.[CH3:46][OH:47].CN([CH:51]=[O:52])C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[CH3:16][O:15][CH2:14][CH2:13][CH2:12][CH2:11][N:8]1[C:9]2[C:5](=[CH:4][CH:3]=[C:2]([C:46]([O:52][CH3:51])=[O:47])[CH:10]=2)[C:6]([CH3:19])([CH3:18])[C:7]1=[O:17]

Participants

Conditions

Temperature: 100 °C

Procedure

To 6-bromo-1-(4-methoxybutyl)-3,3-dimethyl-1,3-dihydro-2H-indol-2-one (1.0 g) were added palladium acetate (207 mg), triphenylphosphine (484 mg), triethylamine (0.86 ml), methanol (0.62 ml), and DMF (10 ml), and the mixture was stirred at 100° C. under carbon monoxide atmosphere for 4 hours. After the reaction was complete, water was added to the reaction solution, and the mixture was extracted with ethyl acetate solution. This ethyl acetate solution was washed with water and an aqueous sodium chloride solution, dried over magnesium sulfate, filtered, and concentrated. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=3/1) to give the title compound (480 mg) as a pale yellow liquid.

Workup

extractionthe mixture was extracted with ethyl acetate solution
washThis ethyl acetate solution was washed with water
dry with materialan aqueous sodium chloride solution, dried over magnesium sulfate
filtrationfiltered
concentrationconcentrated
customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=3/1)

Sources & evidence

ORD record: ord-d9dd2799b6cc48d89fc6374b975df357
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08389511B2

Reaction notes

Loading…