Water → Tert-butyl 4-(4-methylpyridin-2-yl)-1,4-diazepane-1-carboxylate

HRID 1775335Notes

Reaction equation

Br[C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][N:3]=1.[N:9]1([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:15][CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1.C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[CH3:8][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([N:12]2[CH2:13][CH2:14][CH2:15][N:9]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:10][CH2:11]2)[CH:7]=1

Participants

Conditions

Temperature: 140 °C

Procedure

2-Bromo-4-methylpyridine (400 mg, 2.326 mmol), tert-butyl 1,4-diazepane-1-carboxylate (2.1 g, 10.5 mmol) and potassium carbonate (2.8 g, 20 mmol) were combined in anhydrous DMF (20 ml) and heated under microwave heating at 140° C. for 5 hours. The mixture was poured into water and extracted with ethyl acetate (4×). The combined organic layers were washed with brine (2×) and dried over sodium sulfate. The solvent was removed under reduced pressure and the residue was purified two times by column chromatography (silica, gradient from 0 to 50% ethyl acetate in heptane) to yield 97 mg (0.33 mmol, 14%). MS (ESI) m/z=292.2 [M+1]+.

Workup

temperatureheated under microwave
extractionextracted with ethyl acetate (4×)
washThe combined organic layers were washed with brine (2×)
dry with materialdried over sodium sulfate
customThe solvent was removed under reduced pressure
customthe residue was purified two times by column chromatography (silica, gradient from 0 to 50% ethyl acetate in heptane)
customto yield 97 mg (0.33 mmol, 14%)

Sources & evidence

ORD record: ord-9a96c19a6d984daab6827d93e99f5023
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09260441B2

Reaction notes

Loading…