Methyl iodide → HCID 58133382, compound

HRID 1042314Notes

Reaction equation

[Cl:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[C:4]([F:9])[C:3]=1[C:10]1[C:11](=[O:27])[NH:12][C:13]2[C:18]([C:19]=1[O:20][C:21](=[O:26])[C:22]([CH3:25])([CH3:24])[CH3:23])=[CH:17][N:16]=[CH:15][CH:14]=2.C(=O)([O-])[O-].[K+].[K+].CI.[C:36](#N)[CH3:37]>C(OCC)(=O)C.O>[Cl:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[C:4]([F:9])[C:3]=1[C:10]1[C:11](=[O:27])[N:12]([CH2:36][CH3:37])[C:13]2[C:18]([C:19]=1[O:20][C:21](=[O:26])[C:22]([CH3:23])([CH3:24])[CH3:25])=[CH:17][N:16]=[CH:15][CH:14]=2

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 2,2-dimethyl-propionic acid 3-(2-chloro-3,6-difluoro-phenyl)-2-oxo-1,2-dihydro-[1,6]naphthyridin-4-yl ester (250 mg) in acetonitrile (1.5 ml) was added potassium carbonate (88 mg) followed by methyl iodide (51 μl). The reaction mixture was heated to 100° C. for 22 minutes in a microwave and then cooled to ambient temperature. The reaction mixture was diluted with ethyl acetate and water. The phases were separated. The organic fraction was washed with water and brine, dried over magnesium sulfate and concentrated. The residue was purified by column chromatography on silica gel (eluent: ethyl acetate/hexane 1:3 and then 1:1) to give Compound No. B1 of Table B as an orange oil (16 mg). 1H-NMR (400 MHz, CDCl3): 8.84 (s, 1H), 8.71 (d, 1H), 7.32 (d, 1H), 7.18-7.23 (m, 1H), 7.05-7.10 (m, 1H), 4.38 (q, 2H), 1.41 (t, 3H), 1.16 (s, 9H) ppm.

Workup

temperaturecooled to ambient temperature
customThe phases were separated
washThe organic fraction was washed with water and brine
dry with materialdried over magnesium sulfate
concentrationconcentrated
customThe residue was purified by column chromatography on silica gel (eluent
customethyl acetate/hexane 1:3 and then 1:1) to give Compound No

Sources & evidence

ORD record: ord-1735d865ef2b4bd28034c69723272884
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08557840B2

Reaction notes

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