Dimethylformamide → 1-(4-Methoxybenzyl)-2-oxo-1,2-dihydro-3-chloro-4-methoxycarbonyl-5-chloromethyl-pyridine

HRID 1752595Notes

Reaction equation

O=S(Cl)[Cl:3].CN(C=O)C.[CH3:10][O:11][C:12]1[CH:32]=[CH:31][C:15]([CH2:16][N:17]2[CH:22]=[C:21]([CH2:23]O)[C:20]([C:25]([O:27][CH3:28])=[O:26])=[C:19]([Cl:29])[C:18]2=[O:30])=[CH:14][CH:13]=1>C(Cl)(Cl)Cl>[CH3:10][O:11][C:12]1[CH:32]=[CH:31][C:15]([CH2:16][N:17]2[CH:22]=[C:21]([CH2:23][Cl:3])[C:20]([C:25]([O:27][CH3:28])=[O:26])=[C:19]([Cl:29])[C:18]2=[O:30])=[CH:14][CH:13]=1

Participants

Conditions

Temperature: 70 °C

Procedure

SOCl2 (0.1 ml, 1.370 mmol) and DMF (0.1 ml, 1.291 mmol) were each slowly added in sequence to a suspension of compound (11) (360 mg, 1.066 mmol) in CHCl3 (10 ml) and the reaction was stirred at 70° C. for about 3 h. The solvent was removed and the resulting mixture was deposited onto silica gel, loaded onto a silica gel column and eluted with MeOH/DCM (1:100) to afford the title compound (110 mg, 0.309 mmol, 29.0% yield). 1H-NMR (CDCl3, 400 MHz): δ=3.80 (s, 3H), 3.98 (s, 3H), 4.37 (s, 2H), 5.09 (s, 2H), 6.89 (d, 2H, J=8.0 Hz), 7.28 (d, 2H, J=8.0 Hz).

Workup

customThe solvent was removed
washeluted with MeOH/DCM (1:100)

Sources & evidence

ORD record: ord-516cba0ebee34b7ab53d372ce49d0fa8
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09163019B2

Reaction notes

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