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

HRID 1697158Notes

Reaction equation

HRID 1697158 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 added into a three-neck flask (500 mL) under argon. The resulting yellow mixture was refluxed for 2 h. Additional NBS (1.91 g) and benzoyl peroxide (0.021 g) were added. Two hours later, more NBS (0.95 g) and benzoyl peroxide (0.021 g) were added and the mixture was continually refluxed for 3 h. The mixture was then cooled to room temperature. The solution was transferred into another flask and concentrated in vacuo to afford crude 6-(bromomethyl)-2-(2-nitrophenyl)thiazolo[5,4-b]pyridine (4.0 g), which was directly used for next step.

Workup

  1. temperatureThe resulting yellow mixture was refluxed for 2 h
  2. temperaturethe mixture was continually refluxed for 3 h
  3. customThe solution was transferred into another flask
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c35966a0b1b946dca853f6706c65860f
Source dataset
uspto-grants-2012_04
Patent number
US08163908B2

Reaction notes

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