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

HRID 723716Notes

Reaction equation

HRID 723716 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 (0.4g, 1.75 mmol) and iron powder (0.51g, 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-8a62417d22ab4d99b8c219a77f420f03
Source dataset
uspto-grants-2006_11
Patent number
US07141578B2

Reaction notes

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