N-bromobutanimide → 3-bromo-4-fluoro-5-(1-methyl-1H-pyrazol-4-yl)pyridin-2-amine

HRID 595851Notes

Reaction equation

[F:1][C:2]1[C:7]([C:8]2[CH:9]=[N:10][N:11]([CH3:13])[CH:12]=2)=[CH:6][N:5]=[C:4]([NH2:14])[CH:3]=1.C1C(=O)N([Br:22])C(=O)C1>C(#N)C>[Br:22][C:3]1[C:4]([NH2:14])=[N:5][CH:6]=[C:7]([C:8]2[CH:9]=[N:10][N:11]([CH3:13])[CH:12]=2)[C:2]=1[F:1]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 4-fluoro-5-(1-methyl-1H-pyrazol-4-yl)pyridin-2-amine (150 mg, 0.780 mmol) in acetonitrile (7. 805 mL) was added NBS (142 mg, 0.796 mmol) in three portions at 0° C. The reaction mixture was stirred at 0° C. for 20 min. LCMS showed the reaction complete. After quenched with sat Na2SO3 and NaHCO3, stirred for 30 min. The reaction mixture was extracted with EtOAc 3 times. Filtered out solid. The solid was not the desired product. The EtOAc layers were washed by sat NaHCO3, water and brine. Dried and concentrated. The crude material was purified with flash chromatography eluting with 0-100% EtOAc (containing 10% MeOH/heptane to provide 30 mg of desired product. LCMS (m/z): 273.1 (MH+), 0.46 min.

Workup

customthe reaction complete
customAfter quenched with sat Na2SO3 and NaHCO3
stirringstirred for 30 min
extractionThe reaction mixture was extracted with EtOAc 3 times
filtrationFiltered out solid
washThe EtOAc layers were washed
customDried
concentrationconcentrated
customThe crude material was purified with flash chromatography
washeluting with 0-100% EtOAc (
additioncontaining 10% MeOH/heptane

Sources & evidence

ORD record: ord-3b4eb4f2fd06407bb6a0fd71c7d1b625
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09242996B2

Reaction notes

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