2-Fluoro-3-(tributylstannyl)pyridine → HCID 86691832, compound

HRID 1616221Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]2[N:8]([CH3:17])[C:9](=[O:16])[N:10]([CH2:11][C:12]([CH3:15])([CH3:14])[CH3:13])[C:5]2=[CH:4][CH:3]=1.[F:18][C:19]1[C:24]([Sn](CCCC)(CCCC)CCCC)=[CH:23][CH:22]=[CH:21][N:20]=1>CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C>[CH3:13][C:12]([CH3:15])([CH3:14])[CH2:11][N:10]1[C:5]2[C:6](=[N:7][C:2]([C:24]3[C:19]([F:18])=[N:20][CH:21]=[CH:22][CH:23]=3)=[CH:3][CH:4]=2)[N:8]([CH3:17])[C:9]1=[O:16]

Participants

Conditions

Temperature: 90 °C

Procedure

To a microwave vial was added 5-chloro-1-(2,2-dimethylpropyl)-3-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (14-1) (25 mg, 0.1 mmol), 2-fluoro-3-(tributylstannanyl)pyridine (55 mg, 0.15 mmol), and bis(tri-t-butylphosphine)palladium(0) (10 mg, 0.02 mmol). The reagents were purged with nitrogen, dissolved in DMF (0.5 ml), and heated at 90° C. overnight. The reaction was cooled to room temperature, diluted with methanol, and passed through a syringe filter. The solution was purified using reverse phase chromatography (10-100%, 0.1% TFA in H2O/Acetonitrile) and the desired fractions were collected and concentrated to produce 1-(2,2-dimethylpropyl)-5-(2-fluoropyridin-3-yl)-3-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (22-1). HRMS (M+H)+: observed=315.1618, calculated=315.1616.

Workup

customThe reagents were purged with nitrogen
dissolutiondissolved in DMF (0.5 ml)
temperatureThe reaction was cooled to room temperature
additiondiluted with methanol
custompassed through a syringe
filtrationfilter
customThe solution was purified
customthe desired fractions were collected
concentrationconcentrated

Sources & evidence

ORD record: ord-af6b4a06da6c46b7af5f498bad25874a
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765784B2

Reaction notes

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