Stannous Chloride → HCID 22473603, compound

HRID 2183977Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-])=O)=[CH:4][C:3]=1[C:11]1[C:12]([C:17]#[N:18])=[N:13][CH:14]=[CH:15][CH:16]=1.[Sn](Cl)Cl>>[NH2:8][C:5]1[CH:6]=[CH:7][C:2]([F:1])=[C:3]([C:11]2[C:12]([C:17]#[N:18])=[N:13][CH:14]=[CH:15][CH:16]=2)[CH:4]=1

Participants

Reactant 2

HCID 24479Stannous Chloride

HCID 22473591HCID 22473591, compound

Product 1

HCID 22473603HCID 22473603, compound

Procedure

By the method of Example 1, 3-(2-fluoro-5-nitrophenyl)pyridine-2-carbonitrile was reduced with tin(II) chloride to afford 3-(5-amino-2-fluorophenyl)pyridine-2-carbonitrile, which in turn was converted to 3-(5-bromo-2-fluorophenyl)pyridine-2-carbonitrile. Crystallisation from toluene/isohexane furnished off-white needles: δH (400 MHz, CDCl3) 8.77 (1H, dd, J 5 and 2 ), 7.83 (1H, t, J 1.5), 7.59 (3H, m), 7.16 (1H, t, J 9); m/z (ES+) 277, 279.

Sources & evidence

ORD record: ord-6dc25b111cc448fea8e72b56bfbc69f7
Source dataset: uspto-grants-2005_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06900215B2

Reaction notes

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