HCID 21874892, compound → 5-Amino-3-fluoropyridine-2-carbonitrile

HRID 1441858Notes

Reaction equation

HRID 1441858 reaction equation
[C:1]([C:3]1[C:8]([F:9])=[CH:7][C:6]([N+:10]([O-])=O)=[CH:5][N:4]=1)#[N:2].CCOC(C)=O.CC(O)=O>[Fe].CCOCC>[NH2:10][C:6]1[CH:7]=[C:8]([F:9])[C:3]([C:1]#[N:2])=[N:4][CH:5]=1

Participants

5

Reactant 2

HCID 21874892HCID 21874892, compoundHCID 22609514Ethyl acetate acetate

Product 1

HCID 218753655-Amino-3-fluoropyridine-2-carbonitrileYield 94.2%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 3283Diethyl EtherSolvent

Procedure

2-Cyano-3-fluoro-5-nitropyridine (0.12 g, 0.72 mmol) and iron powder (0.21 g, 3.6 mmol, 325 Mesh) were reacted in 1:1 EtOAc/AcOH (10 mL) utilizing the procedure described in example 762D. Trituration of the crude product with ether gave compound 771D (0.093 g, 94%) as a pale yellow solid. HPLC: 99% at 1.27 min(YMC S5 ODS column) eluting with 10-90% aqueous methanol containing 0.2% phosphoric acid over a 4 min gradient monitoring at 220 nm. MS (ES): m/z 138.02 [M+H]+.

Sources & evidence

ORD record
ord-c076171973924b568681cc60552f4fec
Source dataset
uspto-grants-2010_02
Patent number
US07655689B2

Reaction notes

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