N-methyl-2-pyrrolidone → HCID 86687907, compound

HRID 515244Notes

Reaction equation

[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[C:4](F)[N:3]=1.[N:10]1([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1.CN1C(=O)CCC1.CCN(C(C)C)C(C)C>CCOC(C)=O>[Br:1][C:2]1[N:3]=[C:4]([N:13]2[CH2:12][CH2:11][N:10]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:15][CH2:14]2)[CH:5]=[CH:6][C:7]=1[CH3:8]

Participants

Conditions

Temperature: 120 °C

Procedure

To microwave vial was added 2-bromo-6-fluoro-3-methylpyridine (1355 mg, 7.13 mmol), tert-butyl piperazine-1-carboxylate (1338 mg, 7.18 mmol), anhydrous NMP (3.5 mL), and DIPEA (1.65 ml, 9.45 mmol). The resulting mixture was heated at 120° C. for 16 hours. The reaction mixture was allowed to cool to room temperature. The mixture was then diluted with EtOAc (100 mL), washed with water (20 mL) and brine (20 mL), dried over sodium sulfate, filtered and concentrated. The crude residue was purified by flash chromatography (80 g SiO2, 0-25% EtOAc in hexanes) to afford tert-butyl 4-(6-bromo-5-methylpyridin-2-yl)piperazine-1-carboxylate (46-1) as a waxy tan solid. HRMS m/z (M+H) 356.0971 measured, 356.0968 calculated.

Workup

temperatureto cool to room temperature
washwashed with water (20 mL) and brine (20 mL)
dry with materialdried over sodium sulfate
filtrationfiltered
concentrationconcentrated
customThe crude residue was purified by flash chromatography (80 g SiO2, 0-25% EtOAc in hexanes)

Sources & evidence

ORD record: ord-caf62ea94dcd49ff852448d826a1f33e
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09108937B2

Reaction notes

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