Bromine → 5-Methoxy[1,3]thiazolo[5,4-b]pyridin-2-amine

HRID 1965853Notes

Reaction equation

HRID 1965853 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([NH2:9])=[CH:5][CH:4]=1.[C:10]([S-:12])#[N:11].[K+].BrBr>CC(O)=O>[CH3:1][O:2][C:3]1[N:8]=[C:7]2[S:12][C:10]([NH2:11])=[N:9][C:6]2=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 24408BromineHCID 811216-Methoxy-3-pyridinylamineHCID 516872Potassium thiocyanate

Product 1

HCID 28015575-Methoxy[1,3]thiazolo[5,4-b]pyridin-2-amine

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent3×

Procedure

A solution of 6-methoxypyridin-3-amine (2.5 g, 20 mmol) in 5 mL of AcOH was slowly added to a solution of KSCN in 50 mL of AcOH with vigorously stirring at 0 C, followed by a solution of bromine in 3 mL of AcOH. The mixture was stirring at 0 C for 1 h and slowly warmed to rt and stirring was continued for 30 min at rt. Solid was collected via filtration and washed with AcOH (2×20 mL), and partitioned between EtOAc (100 mL) and NaHCO3 (sat. 80 mL). Organic phase was dried over MgSO4 and filtered and the filtrate was concentrated to afford 5-methoxythiazolo[5,4-b]pyridin-2-amine (WZ02129) as a tan solid (2.5 g, 69%). MS (ESI) m/z 182 (M+H+).

Workup

  1. stirringThe mixture was stirring at 0 C for 1 h
  2. stirringstirring
  3. filtrationSolid was collected via filtration
  4. washwashed with AcOH (2×20 mL)
  5. custompartitioned between EtOAc (100 mL) and NaHCO3 (sat. 80 mL)
  6. dry with materialOrganic phase was dried over MgSO4
  7. filtrationfiltered
  8. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-8461dbb2981646f58e480359da58fb74
Source dataset
uspto-grants-2013_04
Patent number
US08420052B2

Reaction notes

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