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

HRID 1667035Notes

Reaction equation

HRID 1667035 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-a2ebbc6cd0a941568268595c20651960
Source dataset
uspto-grants-2011_10
Patent number
US08044198B2

Reaction notes

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