Methyl iodide → HCID 86718140, compound

HRID 2205153Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]([CH3:34])[C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:16]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[N:17][C:18]3[C:23]([N:24]=2)=[CH:22][C:21]([C:25]([OH:27])=[O:26])=[CH:20][CH:19]=3)=[CH:11][CH:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:35]([O-])([O-])=O.[K+].[K+].CI>CN(C=O)C>[C:1]([O:5][C:6]([N:8]([CH3:34])[C:9]1[CH:10]=[CH:11][C:12]([C:15]2[C:16]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[N:17][C:18]3[C:23]([N:24]=2)=[CH:22][C:21]([C:25]([O:27][CH3:35])=[O:26])=[CH:20][CH:19]=3)=[CH:13][CH:14]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 3-(4-(t-butoxycarbonyl(methyl)amino)phenyl)-2-phenylquinoxaline-6-carboxylic acid (213.5 mg, 0.46 mmol, 1.00 equiv, 99%) and K2CO3 (324.2 mg, 2.35 mmol, 5.00 equiv) in DMF (8 mL) was stirred 45 min at room temperature under an inert atmosphere. CH3I (333.7 mg, 2.35 mmol, 5.00 equiv) was added dropwise, with stirring, at 0° C. The resulting solution was stirred for 1 h at room temperature, then quenched by water. The solution was extracted with 5×10 mL of CH2Cl2, and the organic layers combined and dried over anhydrous sodium sulfate. The solids were filtered out, and the resulting mixture was concentrated under vacuum affording 218 mg (98%) of methyl 3-(4-(t-butoxycarbonyl(methyl)amino)phenyl)-2-phenylquinoxaline-6-carboxylate as a yellow solid.

Workup

stirringThe resulting solution was stirred for 1 h at room temperature
customquenched by water
extractionThe solution was extracted with 5×10 mL of CH2Cl2
dry with materialdried over anhydrous sodium sulfate
filtrationThe solids were filtered out
concentrationthe resulting mixture was concentrated under vacuum

Sources & evidence

ORD record: ord-7ad662db1a5440a5bc8fc349ed027f80
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09370522B2

Reaction notes

Loading…