Triethylamine → HCID 58127218, compound

HRID 1963807Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4](F)[N:3]=1.Cl.[O:10]1[CH2:15][CH2:14][CH:13]([CH2:16][NH2:17])[CH2:12][CH2:11]1.CCN(CC)CC>CS(C)=O.CCOC(C)=O>[Br:1][C:2]1[N:3]=[C:4]([NH:17][CH2:16][CH:13]2[CH2:14][CH2:15][O:10][CH2:11][CH2:12]2)[CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of 2-bromo-6-fluoropyridine (750 mg, 4.26 mmol) in DMSO (3 mL) was mixed with (tetrahydro-2H-pyran-4-yl)methanamine hydrochloride (775 mg, 5.11 mmol) and NEt3 (1.426 mL, 10.23 mmol). The resulting mixture was heated at about 110° C. for 18 hr. The mixture was cooled to ambient temperature and diluted with EtOAc. The organic layer was separated, washed with saturated aqueous sodium bicarbonate solution, water, and brine, dried over sodium sulfate, filtered and concentrated in vacuo to yield a resulting residue. 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 providing 6-bromo-N-((tetrahydro-2H-pyran-4-yl)methyl)pyridin-2-amine (B1, 940 mg) as a white solid. LCMS (m/z): 271.0/272.9 [M+H]+; Retention time=0.81 min.

Workup

temperatureThe mixture was cooled to ambient temperature
customThe organic layer was separated
washwashed with saturated aqueous sodium bicarbonate solution, water, and brine
dry with materialdried over sodium sulfate
filtrationfiltered
concentrationconcentrated in vacuo
customto yield a resulting residue
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-12b68753cf264426b16e1ee7f0d01e5e
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08415381B2

Reaction notes

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