Sodium hydride → 2-(6,7-Dimethoxy-quinoxalin-2-yl)-2-aza-bicyclo[2.2.2]octan-3-one

HRID 1859503

Reaction equation

[CH:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[C:3](=[O:9])[NH:2]2.[H-].[Na+].Cl[C:13]1[CH:22]=[N:21][C:20]2[C:15](=[CH:16][C:17]([O:25][CH3:26])=[C:18]([O:23][CH3:24])[CH:19]=2)[N:14]=1>C1COCC1.CN(C=O)C>[CH3:24][O:23][C:18]1[CH:19]=[C:20]2[C:15](=[CH:16][C:17]=1[O:25][CH3:26])[N:14]=[C:13]([N:2]1[C:3](=[O:9])[CH:4]3[CH2:7][CH2:8][CH:1]1[CH2:6][CH2:5]3)[CH:22]=[N:21]2

Participants

Conditions

Temperature: 80 °C

Procedure

2-Azabicyclo[2.2.2]octan-3-one (228 mg, 2.3 mmole) is dissolved in a mixture of THF/DMF (5 mL/3 mL) and treated with NaH (60%, 184 mg, 4.6 mmole). The resulting mixture is heated at 60° C. for 0.5 hour before addition of 2-chloro-6,7-dimethoxyquinoxaline (344 mg, 1.5 mmole). After being heated at 80° C. overnight, the reaction mixture is concentrated . The residue is chromatographed on silica gel (50% ethyl acetate/hexane) to give 164 mg (23%) of a yellow solid (m.p. 158-159° C.).

Workup

concentrationthe reaction mixture is concentrated
customThe residue is chromatographed on silica gel (50% ethyl acetate/hexane)

Sources & evidence

ORD record: ord-6f15a6f2d2d146dab78d904a4fc466f8
Source dataset: uspto-grants-2003_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06528526B1

Linked notes

Loading…