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

HRID 505584Notes

Reaction equation

HRID 505584 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([NH2:9])=[CH:5][CH:4]=1.[S-:10][C:11]#[N:12].[K+].BrBr>C(O)(=O)C>[CH3:1][O:2][C:3]1[N:8]=[C:7]2[S:10][C:11]([NH2:12])=[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×

Conditions

Temperature
0 °C

Procedure

A solution of 6-methoxy-pyridin-3-ylamine (5.0 g, 0.0403 mol) in 10 mL of acetic acid is added slowly to a solution of potassium thiocyanate (20 g, 0.205 mol) in 100 mL of acetic acid at 0° C. followed by a solution of bromine (2.5 mL, 0.0488 mol) in 5 mL of acetic acid. The reaction is stirred for 2 h at 0° C. and then allowed to warm to RT. The resulting solid is collected by filtration and washed with acetic acid, then partitioned between ethyl acetate and saturated aqueous sodium bicarbonate. The insoluble material is removed by filtration and the organic layer is evaporated and dried to afford 5-methoxy-thiazolo[5,4-b]pyridin-2-ylamine as a tan solid.

Workup

  1. temperatureto warm to RT
  2. filtrationThe resulting solid is collected by filtration
  3. washwashed with acetic acid
  4. custompartitioned between ethyl acetate and saturated aqueous sodium bicarbonate
  5. customThe insoluble material is removed by filtration
  6. customthe organic layer is evaporated
  7. customdried

Sources & evidence

ORD record
ord-3cdf78ba52a94fce8c0d70e5b174411d
Source dataset
uspto-grants-2010_08
Patent number
US07781451B2

Reaction notes

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