Water → HCID 23091725, compound

HRID 1182368Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]([CH:20]=O)[C:5]([N:8]([CH2:16][CH:17]([CH3:19])[CH3:18])[CH2:9][CH2:10][CH2:11][C:12]([O:14][CH3:15])=[O:13])=[N:6][CH:7]=1.C[O-].[Na+].O>C(=O)(OC)OC.CO>[Br:1][C:2]1[CH:7]=[N:6][C:5]2[N:8]([CH2:16][CH:17]([CH3:19])[CH3:18])[CH2:9][CH2:10][C:11]([C:12]([O:14][CH3:15])=[O:13])=[CH:20][C:4]=2[CH:3]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of methyl 4-[(5-bromo-3-formylpyridin-2-yl)(isobutyl)amino]butanoate (750 mg) in dimethyl carbonate (20 ml) was added a 28% sodium methoxide solution in methanol (810 mg), and the mixture was heated at 50° C. for 2 hours under a nitrogen atmosphere. The mixture was returned to room temperature, water was added thereto and then extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over magnesium sulfate. The solvent was distilled off under reduced pressure and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=19:1→hexane:ethyl acetate=6:1) to give methyl 3-bromo-9-isobutyl-8,9-dihydro-7H-pyrido[2,3-b]azepine-6-carboxylate (654 mg) as a yellow oily material.

Workup

customwas returned to room temperature
extractionextracted with ethyl acetate
washThe organic layer was washed with saturated brine
dry with materialdried over magnesium sulfate
distillationThe solvent was distilled off under reduced pressure
customthe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=19:1→hexane:ethyl acetate=6:1)

Sources & evidence

ORD record: ord-35163e63def14734a8348e5b611e750b
Source dataset: uspto-grants-2007_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07288654B2

Reaction notes

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