Potassium tert-butoxide → (R)-5-bromo-7-methyl-6-(oxiran-2-yl)quinoline

HRID 2207045Notes

Reaction equation

HRID 2207045 reaction equation
CC1C=CC(S(O[CH2:12][C@@H:13]([C:15]2[C:16]([Br:26])=[C:17]3[C:22](=[CH:23][C:24]=2[CH3:25])[N:21]=[CH:20][CH:19]=[CH:18]3)[OH:14])(=O)=O)=CC=1.CC(C)([O-])C.[K+]>C1COCC1>[Br:26][C:16]1[C:15]([C@@H:13]2[CH2:12][O:14]2)=[C:24]([CH3:25])[CH:23]=[C:22]2[C:17]=1[CH:18]=[CH:19][CH:20]=[N:21]2

Participants

4

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 89676717(R)-2-(5-bromo-7-methylquinolin-6-yl)-2-hydroxyethyl 4-methylbenzenesulfonate

Product 1

HCID 89676992(R)-5-bromo-7-methyl-6-(oxiran-2-yl)quinoline

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (R)-2-(5-bromo-7-methylquinolin-6-yl)-2-hydroxyethyl 4-methylbenzenesulfonate (299 mg, 0.69 mmol) in THF (7.5 mL) at 0° C. was added potassium tert-butoxide (0.76 mL of 1.0 M solution in THF, 0.76 mmol). After stirring for 1 h, the reaction mixture was quenched with saturated aqueous NH4Cl, and then diluted with EtOAc. The organic phase was washed with water and brine, dried over Na2SO4, filtered and concentrated and purified by flash column chromatography (silica gel, 0 to 100% ethyl acetate/hexanes) to give (R)-5-bromo-7-methyl-6-(oxiran-2-yl)quinoline. LCMS-ESI+ (m/z): [M+H]+ calc'd for C12H11BrNO: 264.00; Found: 264.1.

Workup

  1. customthe reaction mixture was quenched with saturated aqueous NH4Cl
  2. additiondiluted with EtOAc
  3. washThe organic phase was washed with water and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by flash column chromatography (silica gel, 0 to 100% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-4bcde02aeca14a3e8c85028f34c2513d
Source dataset
uspto-grants-2016_06
Patent number
US09376392B2

Reaction notes

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