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

HRID 2110478Notes

Reaction equation

HRID 2110478 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-1d4d47d5dcc2446092ad5f0085280875
Source dataset
uspto-grants-2009_04
Patent number
US07517904B2

Reaction notes

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