Water → 3-(Cyclopropylmethoxy)-2-iodo-6-methylsulfonylpyridine

HRID 518406Notes

Reaction equation

[I:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[C:4]([S:9]([CH3:12])(=[O:11])=[O:10])[N:3]=1.Br[CH2:14][CH:15]1[CH2:17][CH2:16]1.C([O-])([O-])=O.[K+].[K+].O>C(#N)C>[CH:15]1([CH2:14][O:8][C:7]2[C:2]([I:1])=[N:3][C:4]([S:9]([CH3:12])(=[O:10])=[O:11])=[CH:5][CH:6]=2)[CH2:17][CH2:16]1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 2-iodo-6-methylsulfonylpyridin-3-ol (500.0 mg, 1.67 mmol), bromomethylcyclopropane (248.4 mg, 1.84 mmol) and K2CO3 (461.3 mg, 33.4 mmol) in ACN (15 mL) was stirred at 80° C. for 4 hrs. Water (30 mL) was added and the mixture was extracted with EtOAc (30 mL×3). The combined organic layers were washed with brine (30 mL), dried over Na2SO4, filtered and concentrated to give the title compound (500.0 mg, 84.8%). 1H NMR (CDCl3, 400 MHz) δ 7.96 (d, J=8.8 Hz, 1H), 7.52 (d, J=8.4 Hz, 1H), 4.09 (d, J=6.8 Hz, 2H), 3.22 (s, 3H), 1.36-1.22 (m, 1H), 0.69-0.57 (m, 2H), 0.43-0.37 (m, 2H). LCMS: 354.0 (M+1)+

Workup

extractionthe mixture was extracted with EtOAc (30 mL×3)
washThe combined organic layers were washed with brine (30 mL)
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-cbaca222dea84f609941eca25eeba7e9
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09115114B2

Reaction notes

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