Water → HCID 86720256, compound

HRID 539576Notes

Reaction equation

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

Participants

Conditions

Temperature: 90 °C

Procedure

A suspension of 3-bromo-5-(1-bromoethyl)pyrazolo[1,5-a]pyridine (I-18, 400 mg, 1.32 mmol), N,5-dimethylpyridin-2-amine (230 mg, 1.98 mmol) and K2CO3 (546 mg, 3.96 mmol) in acetonitrile was heated to 90° C. in a sealed tube for overnight. The reaction mixture was cooled to room temperature and water (10 mL) was added. The aqueous phase was extracted with ethyl acetate (2×10 mL). The combined organic layers were dried over Na2SO4 and solvents were removed under reduced pressure. The resulting crude product was purified by column chromatography over silica gel (petroleum ether/EtOAc, 0-4% EtOAc) to afford 210 mg (46%) of N-(1-(3-bromopyrazolo[1,5-a]pyridin-5-yl)ethyl)-N,5-dimethylpyridin-2-amine (I-19) as a yellow solid. ESI-LC/MS (m/z): [M+H]+ 345.2, [(M+2)+H]+ 347, RT 3.31 min.

Workup

temperatureThe reaction mixture was cooled to room temperature
extractionThe aqueous phase was extracted with ethyl acetate (2×10 mL)
dry with materialThe combined organic layers were dried over Na2SO4 and solvents
customwere removed under reduced pressure
customThe resulting crude product was purified by column chromatography over silica gel (petroleum ether/EtOAc, 0-4% EtOAc)

Sources & evidence

ORD record: ord-f36ce9f16f8e4137a5622a4e7ca2e2d2
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08871754B2

Reaction notes

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