Water → N-(5-Bromothiazolo[5,4-b]pyridin-2-yl)acetamide

HRID 2077539

Reaction equation

HRID 2077539 reaction equation
Br[C:2]1[C:7]([NH2:8])=[CH:6][CH:5]=[C:4]([Br:9])[N:3]=1.[C:10]([N:13]=[C:14]=[S:15])(=[O:12])[CH3:11].O>CC(C)=O>[Br:9][C:4]1[N:3]=[C:2]2[S:15][C:14]([NH:13][C:10](=[O:12])[CH3:11])=[N:8][C:7]2=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 962WaterHCID 128851Acetyl isothiocyanateHCID 8176783-Amino-2,6-dibromopyridine

Product 1

HCID 56763853N-(5-Bromothiazolo[5,4-b]pyridin-2-yl)acetamideYield 121.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
67.5 °C

Procedure

2,6-dibromopyridin-3-amine (4.235 g, 16.8 mmol) was dissolved in acetone and acetyl isothiocyanate (1.85 ml, 21.0 mmol) was added. The flask was fit with a reflux condensor and placed in a preheated oil bath (65-70° C.) and stirred under nitrogen for 2.5 hours. Then, the reaction was cooled to room temperature, poured into water, and filtered. The solid was washed with water, saturated sodium bicarbonate, and water again, and then collected and dried under high vacuum to afford N-(5-bromothiazolo[5,4-b]pyridin-2-yl)acetamide (5.54 g, Yield >100%).

Workup

  1. customplaced in a preheated oil bath
  2. temperatureThen, the reaction was cooled to room temperature
  3. filtrationfiltered
  4. washThe solid was washed with water, saturated sodium bicarbonate, and water again
  5. customcollected
  6. customdried under high vacuum

Sources & evidence

ORD record
ord-b5afa79e6b4742d984f01cd24eb5d381
Source dataset
uspto-grants-2011_04
Patent number
US07928140B2

Linked notes

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