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

HRID 2353339Notes

Reaction equation

HRID 2353339 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-767a867ae2bc42d3a36ea76c32b82b1a
Source dataset
uspto-grants-2010_07
Patent number
US07750020B2

Reaction notes

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