Methyl iodide → 7-bromo-1-methyl-1H-pyrido[2,3-b][1,4]oxazin-2(3H)-one

HRID 331035Notes

Reaction equation

[Br:1][C:2]1[CH:12]=[N:11][C:5]2[O:6][CH2:7][C:8](=[O:10])[NH:9][C:4]=2[CH:3]=1.[C:13](=O)([O-])[O-].[K+].[K+].CI>CC(C)=O>[Br:1][C:2]1[CH:12]=[N:11][C:5]2[O:6][CH2:7][C:8](=[O:10])[N:9]([CH3:13])[C:4]=2[CH:3]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a suspension of 7-bromo-1H-pyrido[2,3-b][1,4]oxazin-2(3H)-one (500 mg, 2.183 mmol) in acetone (8 mL) at RT was added potassium carbonate (905 mg, 6.55 mmol) followed by methyl iodide (0.341 mL, 5.46 mmol). This was heated to 60° C. under nitrogen atmosphere for 3 hours. The reaction mixture was cooled to RT, solvent removed in vacuo. The residue was partitioned between water/ethyl acetate (ca. 25 mL each). The aqueous layer was extracted with ethyl acetate (ca. 25 mL twice). The combined organic layers were dried over MgSO4 and solvent removed in vacuo. The residue was purified on silica gel (eluted with 20-60% ethyl acetate/cyclohexane) to afford the title compound (334 mg). LCMS (A): m/z (M+H)+ 243/245, C8H7BrN2O2 requires 242/244 (acidic).

Workup

temperatureThe reaction mixture was cooled to RT
customsolvent removed in vacuo
customThe residue was partitioned between water/ethyl acetate (ca. 25 mL each)
extractionThe aqueous layer was extracted with ethyl acetate (ca. 25 mL twice)
dry with materialThe combined organic layers were dried over MgSO4 and solvent
customremoved in vacuo
customThe residue was purified on silica gel (eluted with 20-60% ethyl acetate/cyclohexane)

Sources & evidence

ORD record: ord-8ccb0c3c11b8442fb89b6e4a5d96d2f9
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08877742B2

Reaction notes

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