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

HRID 1159471Notes

Reaction equation

HRID 1159471 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 (40.3 mmol, 5.0 g) in 10 mL of acetic acid is added slowly to a solution of potassium thiocyanate (205 mmol, 20 g) in 100 mL of acetic acid at 0° C. followed by a solution of bromine (48.8 mmol, 2.5 mL) 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 EtOAc and saturated aqueous NaHCO3. The insoluble material is removed by filtration and the organic layer is dried and evaporated 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 EtOAc and saturated aqueous NaHCO3
  5. customThe insoluble material is removed by filtration
  6. customthe organic layer is dried
  7. customevaporated

Sources & evidence

ORD record
ord-b914ddcfee294d4fbe3fd3e88035fb8e
Source dataset
uspto-grants-2010_10
Patent number
US07812167B2

Reaction notes

Loading…