Dimethyl Sulfoxide → 1-[1-(Methoxyimino)-2,3-dihydro-1H-inden-5-yl]-2-(pyridin-4-yl)ethane-1,2-dione

HRID 1180531Notes

Reaction equation

CS(C)=O.ClCCl.C(Cl)(=O)C(Cl)=O.[CH3:14][O:15][N:16]=[C:17]1[C:25]2[C:20](=[CH:21][C:22]([CH:26]([OH:35])[CH:27]([OH:34])[C:28]3[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=3)=[CH:23][CH:24]=2)[CH2:19][CH2:18]1>ClCCl.CS(C)=O.C(N(CC)CC)C>[CH3:14][O:15][N:16]=[C:17]1[C:25]2[C:20](=[CH:21][C:22]([C:26](=[O:35])[C:27]([C:28]3[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=3)=[O:34])=[CH:23][CH:24]=2)[CH2:19][CH2:18]1

Participants

Conditions

Temperature: -60 °C

Procedure

To a mixture of DMSO (43 ml, 0.56 mol) and dichloromethane (800 ml) at −70° C. under argon, was added oxalyl chloride (43.2 g) and then a solution of the product of Step 3 (55 g, 0.185 mol) in a mixture of dichloromethane/DMSO (1000 ml/60 ml) over 2 hours at −60° C. After stirring for 2 hours at −60° C., triethylamine (154 ml) was added dropwise and the mixture then allowed to warm to room temperature overnight. The reaction mixture was then quenched with water, the organic phase separated then washed with water, dried (Na2SO4) and concentrated to yield the title compound (51 g, 94%) as a yellow solid. 1H NMR (CDCl3) 8.87 (2H, d), 7.89-7.77 (5H, m), 4.03 (3H, s), 3.09 (2H,m), 2.93 (2H, m).

Workup

temperatureto warm to room temperature overnight
customThe reaction mixture was then quenched with water
customthe organic phase separated
washthen washed with water
dry with materialdried (Na2SO4)
concentrationconcentrated

Sources & evidence

ORD record: ord-d51d2c4728904ce190fa87ff3d11cf41
Source dataset: uspto-grants-2007_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07282500B2

Reaction notes

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