Methyl iodide → HCID 66997792, compound

HRID 2066610Notes

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-e6ad649b78994537aba9dfd829a65aff
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08293731B2

Reaction notes

Loading…