Methyl iodide → HCID 22947429, compound

HRID 1028227Notes

Reaction equation

[F:1][C:2]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][C:3]=1[NH:4][C:5](=[O:10])[C:6]([F:9])([F:8])[F:7].CI.[C:20]([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[F:1][C:2]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][C:3]=1[N:4]([CH3:20])[C:5](=[O:10])[C:6]([F:7])([F:8])[F:9]

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of compound 32-NO2—H (13.9 g, 55.2 mmol) and MeI (14.8 g, 0.104 mol) in DMF (80 mL), K2CO3 (12.5 g, 90.6 mmol) was added. After vigorous stirring for 24 h at 90° C., volatile materials were evaporated in vacuum. The residue was diluted with water (200 mL), the organic layer was separated, and the aqueous layer was extracted with ether (3×100 mL). Combined organic solutions were dried, and the solvent was evaporated at an ambient pressure (bath temperature 50° C.). The title compound was isolated by chromatography on SiO2 (600 g) with hexane/EtOAc mixture (1:0→1:1) as an eluent; yellowish oil (13.6 g, purity ca. 90%, yield 83%). 1H NMR (CDCl3, 300 MHz, ppm): δ=3.36 (s, 3 H, CH3), 7.39 (t, 3JHH=JHF=8.8, 1H, H-3), 8.25 (dd, 4JHH=2.6, 4JHF=6.5, 1H, H-6), 8.32-8.38 (m, 1H, H-4); EI-MS: m/z (rel. int., %)=266 (100) [M], 197 (57) [M-CF3], 184 (32), 170 (23), 123 (37), 110 (18).

Workup

customvolatile materials were evaporated in vacuum
additionThe residue was diluted with water (200 mL)
customthe organic layer was separated
extractionthe aqueous layer was extracted with ether (3×100 mL)
customCombined organic solutions were dried
customthe solvent was evaporated at an ambient pressure (bath temperature 50° C.)

Sources & evidence

ORD record: ord-6471b327a27749fa8cd074acb1ff5119
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08735444B2

Reaction notes

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