Methyl iodide → HCID 12069575, compound

HRID 2117369Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:26]=[CH:27][C:28]=1[N+:29]([O-:31])=[O:30])[C:6]([C:8]1[N:16]2[C:11]([CH:12]=[CH:13][CH:14]=[CH:15]2)=[C:10]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[C:9]=1[CH3:25])=[O:7].[H-].[Na+].CI.[C:36](=O)(O)[O-].[Na+]>O1CCCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:26]=[CH:27][C:28]=1[N+:29]([O-:31])=[O:30])[C:6]([C:8]1[N:16]2[C:11]([CH:12]=[CH:13][CH:14]=[CH:15]2)=[C:10]([N:17]([CH3:36])[C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:21])[CH3:22])[C:9]=1[CH3:25])=[O:7]

Participants

Conditions

Temperature: 0 °C

Procedure

3.05 g (7.2 mmol) of tert-butyl 3-(3-methoxy-4-nitrobenzoyl)-2-methylindolizin-1-ylcarbamate in solution in 50 ml of tetrahydrofuran are added dropwise to 315 mg (7.9 mmol) of sodium hydride (at 60% as a dispersion in oil) in suspension in 10 ml of tetrahydrofuran, cooled to 0° C. After stirring for 1 hour at 0° C., 0.59 ml (9.5 mmol) of methyl iodide is added while the medium is maintained at 0° C. It is allowed to return to room temperature and it is stirred for 1 hour. The reaction medium is poured over a saturated aqueous sodium bicarbonate solution and extracted with ethyl acetate. The organic phase is separated after settling out, washed with a saturated aqueous sodium chloride solution, dried over sodium sulphate and concentrated under reduced pressure. 3.47 g of an orange-coloured foam are obtained.

Workup

temperatureis maintained at 0° C
customto return to room temperature
stirringit is stirred for 1 hour
extractionextracted with ethyl acetate
customThe organic phase is separated
washwashed with a saturated aqueous sodium chloride solution
dry with materialdried over sodium sulphate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-a0c3d68451b54cdeb85cb007f15256db
Source dataset: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07442708B2

Reaction notes

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