Methyl iodide → HCID 59283117, compound

HRID 1965840Notes

Reaction equation

[N+:1]([C:4]1[CH:5]=[C:6]([C:10]2[CH:11]=[C:12]3[N:17]([CH:18]=2)[CH:16]=[C:15]([C:19]([NH2:21])=[O:20])[CH:14]=[CH:13]3)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[H-].[Na+].[CH3:24]I>CN(C=O)C.C1COCC1>[CH3:24][NH:21][C:19]([C:15]1[CH:14]=[CH:13][C:12]2[N:17]([CH:18]=[C:10]([C:6]3[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=3)[CH:11]=2)[CH:16]=1)=[O:20]

Participants

Conditions

Temperature: 0 °C

Procedure

To a cooled solution of 2-(3-nitrophenyl)indolizine-6-carboxamide (0.4 g, 1.42 mmol) in DMF/THF (20/10 ml) was added NaH (60% in mineral oil, 58 mg, 1.45 mmol). The resulting mixture was stirred under Ar at 0° C. for 5 min, and then MeI (0.13 mL, 2.08 mmol) was added. The reaction mixture was stirred under Ar at 0° C. and warmed gradually to room temperature and stirred at room temperature overnight. It was concentrated in vacuo. The residue was recrystallized from CH2Cl2/acetone/EtOAc to give a white solid (0.1 g, 24%). 1H NMR (CDCl3, 400 MHz) δ: 8.78 (s, 1H), 8.48 (t, J=2.0 Hz, 1H), 8.42 (br s, 1H), 8.30 (d, J=1.6 Hz, 1H), 8.18 (d, J=7.6 Hz, 1H), 8.09 (dd, J=8.0, 1.6 Hz, 1H), 7.69 (t, J=8.0 Hz, 1H), 7.45 (d, J=9.2 Hz, 1H), 7.13 (dd, J=9.6, 1.6 Hz, 1H), 6.99 (s, 1H), 2.77 (d, J=4.4 Hz, 3H). MS: m/z=296 (M+H+).

Workup

stirringThe reaction mixture was stirred under Ar at 0° C.
temperaturewarmed gradually to room temperature
stirringstirred at room temperature overnight
concentrationIt was concentrated in vacuo
customThe residue was recrystallized from CH2Cl2/acetone/EtOAc

Sources & evidence

ORD record: ord-b79ff99e043b4fe5a5e6549777646556
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08420052B2

Reaction notes

Loading…