Methyl iodide → HCID 66997792, compound

HRID 18032Notes

Reaction equation

[CH2:1]([N:4]1[C:13](=[O:14])[C:12]([OH:15])=[C:11]2[C:6]([CH2:7][CH2:8][N:9]([CH2:17][C:18]3[CH:23]=[CH:22][C:21]([F:24])=[C:20]([Cl:25])[CH:19]=3)[C:10]2=[O:16])=[C:5]1[C:26]([O:28][CH3:29])=[O:27])[CH:2]=[CH2:3].[C:30](=O)([O-])[O-].[Cs+].[Cs+].IC>CN(C=O)C>[CH2:1]([N:4]1[C:13](=[O:14])[C:12]([O:15][CH3:30])=[C:11]2[C:6]([CH2:7][CH2:8][N:9]([CH2:17][C:18]3[CH:23]=[CH:22][C:21]([F:24])=[C:20]([Cl:25])[CH:19]=3)[C:10]2=[O:16])=[C:5]1[C:26]([O:28][CH3:29])=[O:27])[CH:2]=[CH2:3]

Participants

Conditions

Temperature: 40 °C

Procedure

A mixture of methyl 2-(allyl)-6-(3-chloro-4-fluorobenzyl)-4-hydroxy-3,5-dioxo-2,3,5,6,7,8-hexahydro-2,6-naphthyridine-1-carboxylate (6.08 g, 14.92 mmol), cesium carbonate (6.08 g, 18.65 mmol), and iodomethane (2.79 mL, 44.77 mmol) in DMF (20 mL) was heated at 40° C. overnight. The reaction mixture was filtered and concentrated under vacuum. The residue was subjected to column chromatography on silica gel. Collection and concentration of appropriate fractions provided the title compound. (ES MS M+1=435.2)

Workup

filtrationThe reaction mixture was filtered
concentrationconcentrated under vacuum
customCollection and concentration of appropriate fractions

Sources & evidence

ORD record: ord-5311e1db5a0e47a1ad5f583ad17cc237
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07741315B2

Reaction notes

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