Potassium Carbonate → HCID 86650634, compound

HRID 1963935Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[N:3]=1.Cl.[C@H:10]1([NH2:18])[C:12]2([CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[CH2:11]1.C(=O)([O-])[O-].[K+].[K+]>CN1C(=O)CCC1.CCOC(C)=O>[Br:8][C:4]1[N:3]=[C:2]([NH:18][C@H:10]2[C:12]3([CH2:17][CH2:16][O:15][CH2:14][CH2:13]3)[CH2:11]2)[CH:7]=[CH:6][CH:5]=1

Participants

Conditions

Temperature: 110 °C

Procedure

To a solution of 2,6-dibromopyridine (200 mg, 0.84 mmol) in NMP (0.42 mL) was added (R)-6-oxaspiro[2.5]octan-1-amine hydrochloride (138 mg, 0.84 mmol) and potassium carbonate (350 mg, 2.53 mmol). The mixture was heated at 110° C. for 18 hr. The mixture was allowed to cool to ambient temperature and diluted with EtOAc. The organic layer was washed with saturated aqueous sodium bicarbonate solution, water, and brine and dried over sodium sulfate, filtered off and concentrated in vacuo. The resulting residue was purified by column chromatography [SiO2, 40 g, EtOAc/heptane= 0/100 to 30/70]. Pure fractions were combined and concentrated in vacuo giving 210 mg of titled compound. LCMS (m/z): 282.9/284.9 [M+H]+, retention time=0.85 min.

Workup

temperatureto cool to ambient temperature
washThe organic layer was washed with saturated aqueous sodium bicarbonate solution, water, and brine
dry with materialdried over sodium sulfate
filtrationfiltered off
concentrationconcentrated in vacuo
customThe resulting residue was purified by column chromatography [SiO2, 40 g, EtOAc/heptane= 0/100 to 30/70]
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-3182cdca39c6419c8a7f8fcbadcf0f3d
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08415381B2

Reaction notes

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