Methyl iodide → HCID 70664913, compound

HRID 1403654Notes

Reaction equation

[CH:1]1([NH:5][C:6]2[C:7]([C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=3)=[N:8][C:9]3[C:14]([N:15]=2)=[CH:13][C:12]([C:16]([O:18][CH3:19])=[O:17])=[CH:11][CH:10]=3)[CH2:4][CH2:3][CH2:2]1.[H-].[Na+].[CH3:29]I>O1CCCC1>[CH:1]1([N:5]([CH3:29])[C:6]2[C:7]([C:20]3[CH:21]=[CH:22][C:23]([F:26])=[CH:24][CH:25]=3)=[N:8][C:9]3[C:14]([N:15]=2)=[CH:13][C:12]([C:16]([O:18][CH3:19])=[O:17])=[CH:11][CH:10]=3)[CH2:2][CH2:3][CH2:4]1

Participants

Conditions

Temperature: 10 °C

Procedure

To a solution of methyl 3-(cyclobutylamino)-2-(4-fluorophenyl)quinoxaline-6-carboxylate (67 mg, 0.19 mmol) in tetrahydrofuran (20 mL) was added sodium hydride (30 mg, 60%) and CH3I (135 mg, 0.95 mmol). The resulting solution was stirred overnight at 10° C. The reaction was then quenched by the addition of NH4Cl solution (50 mL), extracted with ethyl acetate (4×20 mL), and the organic layers combined, dried over anhydrous magnesium sulfate, and concentrated in vacuo to give a residue, which was purified via silica gel column chromatography (2%-10% ethyl acetate in petroleum ether) to afford methyl 3-[cyclobutyl(methyl)amino]-2-(4-fluorophenyl)quinoxaline-6-carboxylate as a yellow solid (70 mg, crude).

Workup

customThe reaction was then quenched by the addition of NH4Cl solution (50 mL)
extractionextracted with ethyl acetate (4×20 mL)
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated in vacuo
customto give a residue, which
customwas purified via silica gel column chromatography (2%-10% ethyl acetate in petroleum ether)

Sources & evidence

ORD record: ord-7dbfe952ebf74d03ae2bbf1765bded88
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08912188B2

Reaction notes

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