Water → 2-Benzamido-5-bromo-[1,3]thiazolo[5,4-b]pyridine

HRID 241015Notes

Reaction equation

HRID 241015 reaction equation
[Br:1][C:2]1[N:7]=[C:6](Cl)[C:5]([NH:9][C:10]([NH:12][C:13](=[O:20])[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[S:11])=[CH:4][CH:3]=1.[O-]CC.[Na+].O>CN1CCCC1=O>[Br:1][C:2]1[N:7]=[C:6]2[S:11][C:10]([NH:12][C:13](=[O:20])[C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[N:9][C:5]2=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 2723922Sodium ethoxideHCID 86647817N-(6-bromo-2-chloropyridin-3-ylcarbamothioyl)benzamide

Product 1

HCID 457894382-Benzamido-5-bromo-[1,3]thiazolo[5,4-b]pyridineYield 76.3%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of N-(6-bromo-2-chloropyridin-3-ylcarbamothioyl)benzamide (1.5 g, 4.0 mmol) and sodium ethoxide (0.54 g, 8.0 mmol) in 1-methyl-2-pyrrolidinone (10 mL) was heated to 120° C. for 8 hours. After cooling the reaction mixture to room temperature the mixture was poured into water. The resulting solid was collected by filtration, then washed sequentially with water and diethyl ether. The filter cake was dried to give N-(5-bromothiazolo[5,4-b]pyridin-2-yl)benzamide (1.02 g, 76%). 1H NMR (400 MHz, d6-DMSO): 13.2 (br s, 1H), 8.16-8.10 (m, 3H), 7.72 (d, 1H), 7.70 (t, 1H), 7.59 (t, 2H). MS (EI) for C13H8BrN3OS: 336 (MH+).

Workup

  1. filtrationThe resulting solid was collected by filtration
  2. washwashed sequentially with water and diethyl ether
  3. customThe filter cake was dried

Sources & evidence

ORD record
ord-d34c35e9b31f403cab884f11cb72162e
Source dataset
uspto-grants-2014_02
Patent number
US08648066B2

Reaction notes

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