Tributylstannane → N-Acetyl-5-methoxy-3,4,6-trimethylindoline

HRID 1488454Notes

Reaction equation

[CH2:1]([N:4]([C:8]1[CH:13]=[C:12]([CH3:14])[C:11]([O:15][CH3:16])=[C:10]([CH3:17])[C:9]=1Br)[C:5](=[O:7])[CH3:6])[CH:2]=[CH2:3].C([SnH](CCCC)CCCC)CCC.N(C(C)(C)C#N)=NC(C)(C)C#N>C1(C)C=CC=CC=1>[C:5]([N:4]1[C:8]2[C:13](=[C:12]([CH3:14])[C:11]([O:15][CH3:16])=[C:10]([CH3:17])[CH:9]=2)[CH:2]([CH3:3])[CH2:1]1)(=[O:7])[CH3:6]

Participants

Conditions

Temperature: 60 °C

Procedure

A solution of N-allyl-4-acetamido-3-bromo-2,6-dimethylanisole (8, 1.1 g, 3.6 mmol) in dry toluene (237 mL) and tri-n-butylstannane (1.9 mL, 7.1 mmol) was placed in a round-bottom flask fitted with a reflux condenser and slowly warmed to 60° C. under a nitrogen atmosphere. A catalytic amount of azobisisobutyronitrile was added, and the resulting mixture was heated and stirred at 85° C. for 15 h. The cooled reaction mixture was washed sequentially with 1% aq. ammonia and brine, and dried (MgSO4). Removal of solvents gave a liquid which was further purified by flash column chromatography using sequentially hexane and 1:3 ethyl acetate:hexanes as eluents to yield the indoline 9 (790 mg, 95% yield) as a colorless liquid. Spectral data: 13C NMR: δ 11.9, 16.4, 20.5, 23.9, 33.9, 57.3, 59.8, 116.5, 126.3, 129.7, 133.9, 137.6, 153.1, 168.2; HRMS: calcd. for C14H20NO2 (M+H+) 234.1494, fnd. 234.1487.

Workup

customfitted with a reflux condenser
temperaturethe resulting mixture was heated
customThe cooled reaction mixture
washwas washed sequentially with 1% aq. ammonia and brine
dry with materialdried (MgSO4)
customRemoval of solvents
customgave a liquid which
customwas further purified by flash column chromatography

Sources & evidence

ORD record: ord-4c54a5bc28594702a87ac0e3d719551a
Source dataset: uspto-grants-1997_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05674876

Reaction notes

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