Sodium Acetate → 1-(3,3-Dimethyl-6-nitroindolin-1-yl)ethanone

HRID 2109622Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[N:11]([CH2:15][C:16]([CH3:18])=[CH2:17])[C:12](=[O:14])[CH3:13].C([O-])=O.[Na+].C([O-])(=O)C.[Na+]>CN(C=O)C.[Cl-].C([N+](CC)(CC)CC)C>[CH3:17][C:16]1([CH3:18])[C:2]2[C:3](=[CH:4][C:5]([N+:8]([O-:10])=[O:9])=[CH:6][CH:7]=2)[N:11]([C:12](=[O:14])[CH3:13])[CH2:15]1

Participants

Conditions

Temperature: 80 °C

Procedure

N-(2-Bromo-5-nitrophenyl)-N-(2-methylprop-2-enyl) acetamide (4.5 g, Step B) was dissolved in 50 mL anhydrous DMF, 2.5 g tetraethyl-ammonium chloride, 1.2 g sodium formate, 3 g sodium acetate were added, the resulting mixture was bubbled with nitrogen gas for 10 min. Pd(OAc)2 (350 mg) was added and the mixture was heated at 80° C. under N2 overnight. After the mixture was concentrated in vacuo, it was extracted between saturated NaHCO3 solution and EtOAc, the resulting organic layer was dried over MgSO4, filtered and concentrated in vacuo. The crude material was purified by flash chromatography on silica gel with 2:1 Hexane:EtOAc to afford a yellow gum. MS: 235 (M+1). Calc'd. for C12H14N2O3−234.2.

Workup

customthe resulting mixture was bubbled with nitrogen gas for 10 min
additionPd(OAc)2 (350 mg) was added
concentrationAfter the mixture was concentrated in vacuo, it
extractionwas extracted between saturated NaHCO3 solution and EtOAc
dry with materialthe resulting organic layer was dried over MgSO4
filtrationfiltered
concentrationconcentrated in vacuo
customThe crude material was purified by flash chromatography on silica gel with 2:1 Hexane
customEtOAc to afford a yellow gum

Sources & evidence

ORD record: ord-b05bc43d9d6b48f0b4e612e2cdb2135e
Source dataset: uspto-grants-2009_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07514564B2

Reaction notes

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