Dimethylformamide → Tert-butyl 4-(5-bromopyrazin-2-yloxy)piperidine-1-carboxylate

HRID 1666551Notes

Reaction equation

C(=O)([O-])[O-].[Cs+].[Cs+].CN(C=O)C.[Br:12][C:13]1[CH:18]=[N:17][C:16]([OH:19])=[CH:15][N:14]=1.[C:20]([O:24][C:25]([N:27]1[CH2:32][CH2:31][CH:30](OS(C)(=O)=O)[CH2:29][CH2:28]1)=[O:26])([CH3:23])([CH3:22])[CH3:21]>O>[C:20]([O:24][C:25]([N:27]1[CH2:32][CH2:31][CH:30]([O:19][C:16]2[CH:15]=[N:14][C:13]([Br:12])=[CH:18][N:17]=2)[CH2:29][CH2:28]1)=[O:26])([CH3:23])([CH3:21])[CH3:22]

Participants

Conditions

Temperature: 90 °C

Procedure

Cesium carbonate (372 mg) was added to a DMF solution (2 ml) of 2-bromo-5-hydroxypyrazine (100 mg) and 1-t-butoxycarbonyl-4-(methanesulfonyloxy)piperidine (192 mg), and stirred at 90° C. for 14 hours. The reaction mixture was cooled to room temperature, water was added thereto and extracted with ethyl acetate. The organic layer was washed with saturated saline solution, dried with anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified through silica gel column chromatography (C-300, hexane:ethyl acetate=1:11) to obtain the entitled compound (198 mg).

Workup

temperatureThe reaction mixture was cooled to room temperature
extractionextracted with ethyl acetate
washThe organic layer was washed with saturated saline solution
dry with materialdried with anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified through silica gel column chromatography (C-300, hexane:ethyl acetate=1:11)

Sources & evidence

ORD record: ord-33d126b29dd34a709777559deb4793ff
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08044070B2

Reaction notes

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