HCID 21874993, compound → 5-Amino-3-bromo-2-pyridinecarbonitrile

HRID 1441856Notes

Reaction equation

HRID 1441856 reaction equation
[Br:1][C:2]1[C:3]([C:11]#[N:12])=[N:4][CH:5]=[C:6]([N+:8]([O-])=O)[CH:7]=1>[Fe].CCOCC>[NH2:8][C:6]1[CH:7]=[C:2]([Br:1])[C:3]([C:11]#[N:12])=[N:4][CH:5]=1

Participants

4

Reactant 1

HCID 21874993HCID 21874993, compound

Product 1

HCID 218752405-Amino-3-bromo-2-pyridinecarbonitrile

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 3283Diethyl EtherSolvent

Procedure

3-Bromo-2-cyano-5-nitropyridine (0.4 g, 1.75 mmol) and iron powder (0.51 g, 8.8 mmol, 325 Mesh) were reacted as described in example 762D. The crude solid obtained by trituration with ether was purified by SiO2 Prep-TLC using 4:1 CH2Cl2/ether as eluent to give compound 769A (0.16 g, (65%) as an off-white solid. HPLC: 100% at 1.77 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 197.93 [M+H]+.

Workup

  1. customwas purified by SiO2 Prep-TLC

Sources & evidence

ORD record
ord-fcd2257e991e497b96f66790d3d8a7e5
Source dataset
uspto-grants-2010_02
Patent number
US07655689B2

Reaction notes

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