Potassium Carbonate → Methyl 2-((5-methoxy-6-nitropyridin-2-yl)methylthio)acetate

HRID 72660

Reaction equation

HRID 72660 reaction equation
Br[CH2:2][C:3]1[N:8]=[C:7]([N+:9]([O-:11])=[O:10])[C:6]([O:12][CH3:13])=[CH:5][CH:4]=1.C[CH:15]([SH:19])[C:16]([O-:18])=[O:17].[C:20](=O)([O-])[O-].[K+].[K+]>CO>[CH3:13][O:12][C:6]1[CH:5]=[CH:4][C:3]([CH2:2][S:19][CH2:15][C:16]([O:18][CH3:20])=[O:17])=[N:8][C:7]=1[N+:9]([O-:11])=[O:10]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 144051243-Methoxy-2-nitro-6-pyridylmethyl bromideHCID 156077362-Mercaptopropionate

Product 1

HCID 67994824Methyl 2-((5-methoxy-6-nitropyridin-2-yl)methylthio)acetate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 6-(bromomethyl)-3-methoxy-2-nitropyridine (30 mmol, 0.74 g), methythioglycolate (2.7 mL, 30 mmol), and potassium carbonate (5.5 g, 40 mmol) in methanol (200 mL) was stirred at room temperature for 10 hours. After concentrated the mixture was purified by column chromatography using PE/DCM (1:1, v/v) followed by DCM to the titled compound. 1H-NMR (CDCl3): δ 3.27 (S, 2H, CH2), 3.74 (S, 3H, OCH3), 3.93 (S, 2H, CH2), 3.99 (S, 3H, OCH3), 7.51 (d, 1H, J=8.6 Hz, Py-H), 7.65 (d, 1H, J=8.6 Hz, Py-H); HR-MS (ESI+) m/z 272.0467 [M+H]+ C10H12N2O5S requires 273.0547.

Workup

  1. concentrationAfter concentrated the mixture
  2. customwas purified by column chromatography

Sources & evidence

ORD record
ord-41f55f15631d41559d11993553177430
Source dataset
uspto-grants-2014_09
Patent number
US08829003B2

Linked notes

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