Sulfonium → 3-Bromo-4-(oxetan-2-YL)pyridine

HRID 1253944Notes

Reaction equation

HRID 1253944 reaction equation
[CH3:1]C(C)([O-])C.[K+].[SH3+].[Br:8][C:9]1[CH:10]=[N:11][CH:12]=[CH:13][C:14]=1[CH:15]1[CH2:17][O:16]1>CC(O)(C)C.CS(C)=O>[Br:8][C:9]1[CH:10]=[N:11][CH:12]=[CH:13][C:14]=1[CH:15]1[CH2:17][CH2:1][O:16]1

Participants

6

Reactant 3

HCID 3015009SulfoniumHCID 23665647Potassium tert-butoxideHCID 866633603-Bromo-4-(oxiran-2-yl)pyridine

Product 1

HCID 667870223-Bromo-4-(oxetan-2-YL)pyridineYield 44.9%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6386tert-ButanolSolvent

Conditions

Temperature
50 °C

Procedure

potassium tert-butoxide (561 mg, 5 mmol) was added to a solution of sulfonium salt (1100 mg, 5 mmol) in t-BuOH (20 mL) at room temperature. After 15 min, a solution of 3-Bromo-4-oxiranyl-pyridine (200 mg, obtained above) in DMSO (10 mL) was added dropwise at 50° C. The resulting mixture was stirred at 50° C. for 15 h. The reaction mixture was quenched with brine, and the resulting mixture was extracted with ethyl acetate twice. The combined extracts were dried over anhydrous Na2SO4. After filtration and concentration, the residue was purified by flash column and afforded the title compound (96 mg). ESI-MS m/z: 216.1 [M+1]+, Retention time 1.01 min; 1HNMR (CDCl3, 400.342 MHz) δ ppm 2.50-2.59 (m, 1H), 3.31-3.39 (m, 1H), 4.65-4.70 (m, 1H), 4.87-4.92 (m, 1H), 5.91 (t, J=8 Hz, 1H), 7.95 (d, J=8 Hz, 1H), 8.68 (d, J=8 Hz, 1H), 8.73 (s, 1H).

Workup

  1. customThe reaction mixture was quenched with brine
  2. extractionthe resulting mixture was extracted with ethyl acetate twice
  3. dry with materialThe combined extracts were dried over anhydrous Na2SO4
  4. filtrationAfter filtration and concentration
  5. customthe residue was purified by flash column

Sources & evidence

ORD record
ord-2793e48adcfb451190f62c7fdb672034
Source dataset
uspto-grants-2013_06
Patent number
US08455522B2

Reaction notes

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