Bromine → 3-Bromoisothiazolo[5,4-b]pyridine

HRID 502589Notes

Reaction equation

HRID 502589 reaction equation
[S:1]=[C:2]1[C:7]([C:8]#[N:9])=[CH:6][CH:5]=[CH:4][NH:3]1.[Br:10]Br>C(OCC)(=O)C>[Br:10][C:8]1[C:7]2[C:2](=[N:3][CH:4]=[CH:5][CH:6]=2)[S:1][N:9]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 43864192-Sulfanylpyridine-3-carbonitrile

Product 1

HCID 574365573-Bromoisothiazolo[5,4-b]pyridine

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-thioxo-1,2-dihydropyridine-3-carbonitrile (2.1 g, 15.44 mmol) in ethyl acetate (50 mL), bromine (5.9 g, 37.11 mmol) was added drop wise at 0° C. The reaction mixture was allowed to warm to room temperature and then refluxed for 3 h. The reaction mixture was concentrated under reduced pressure. Trituration with hexanes:methylene chloride (1:1) mixture gave 3-bromoisothiazolo[5,4-b]pyridine, as light brown solid which was carried forward without further purification. MW=215 confirmed by LC-MS, tr=16.08 min (Method Y) MH+=216.

Workup

  1. temperaturerefluxed for 3 h
  2. concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-34f2de970d8546c1a365986bc6cc1012
Source dataset
uspto-grants-2010_08
Patent number
US07776847B2

Reaction notes

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