N-bromobutanimide → 6-(Bromomethyl)-2-(2-nitrophenyl)thiazolo[5,4-b]pyridine

HRID 2387401Notes

Reaction equation

HRID 2387401 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[N:10]=[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[N+:17]([O-:19])=[O:18])[S:8][C:5]2=[N:6][CH:7]=1.[Br:20]N1C(=O)CCC1=O>C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.C(Cl)(Cl)(Cl)Cl>[Br:20][CH2:1][C:2]1[CH:3]=[C:4]2[N:10]=[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[N+:17]([O-:19])=[O:18])[S:8][C:5]2=[N:6][CH:7]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimide3×HCID 596798586-Methyl-2-(2-nitrophenyl)thiazolo[5,4-b]pyridine

Product 1

HCID 596801456-(Bromomethyl)-2-(2-nitrophenyl)thiazolo[5,4-b]pyridineYield 106.8%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalyst3×HCID 5943Carbon TetrachlorideSolvent

Procedure

6-Methyl-2-(2-nitrophenyl)thiazolo[5,4-b]pyridine (2.9 g, 10.7 mmol), N-bromosuccinimide (NBS, 1.91 g, 10.7 mmol), CCl4 (200 mL) and benzoyl peroxide (0.021 g) were combined in a three-neck flask (500 mL) under argon. The resulting yellow mixture was stirred at reflux (2 h). Additional NBS (1.91 g) and benzoyl peroxide (0.021 g) were added. After an additional 2 h at reflux, NBS (0.95 g) and benzoyl peroxide (0.021 g) were again added and the mixture was refluxed for 3 h. The mixture was allowed to cool to room temperature and concentrated in vacuo to afford crude 6-(bromomethyl)-2-(2-nitrophenyl)thiazolo[5,4-b]pyridine (4.0 g), which was taken directly to the next step.

Workup

  1. temperatureat reflux (2 h)
  2. temperatureAfter an additional 2 h at reflux
  3. temperaturethe mixture was refluxed for 3 h
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3bd76e4006cc4c158bd27d200fb041e9
Source dataset
uspto-grants-2012_09
Patent number
US08268862B2

Reaction notes

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