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

HRID 2247266Notes

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+].CC([O-])=O.[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 anhydrous DMF (50 mL), tetraethyl-ammonium chloride (2.5 g), sodium formate (1.2 g), NaOAc (3 g) were added, and the resulting mixture was bubbled with N2 gas for 10 min. Pd(OAc)2 (350 mg) was added and the mixture was heated at 80° C. under N2 atmosphere overnight. After the mixture was concentrated in vacuo, it was partitioned 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 the title compound as a yellow gum.

Workup

customthe resulting mixture was bubbled with N2 gas for 10 min
additionPd(OAc)2 (350 mg) was added
concentrationAfter the mixture was concentrated in vacuo, it
customwas partitioned 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

Sources & evidence

ORD record: ord-514b899448034186ab95f8e5ce77dfc2
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07687643B2

Reaction notes

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