Water → HCID 23160371, compound

HRID 2059815Notes

Reaction equation

HRID 2059815 reaction equation
[F:1][C:2]1[N:7]=[CH:6][C:5]([NH2:8])=[CH:4][CH:3]=1.[C:9]([S-:11])#[N:10].[K+].BrBr.O>C(O)(=O)C>[F:1][C:2]1[N:7]=[C:6]2[S:11][C:9]([NH2:10])=[N:8][C:5]2=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24408Bromine3×HCID 516872Potassium thiocyanateHCID 8194405-Amino-2-fluoropyridine

Product 1

HCID 23160371HCID 23160371, compoundYield 69.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

6-Fluoropyridin-3-amine (4 g, 35.7 mmol) was added to a mechanically stirred suspension of potassium rhodanate (27.7 g, 285 mmol) in acetic acid (89 mL) at 0° C. The flask 3-neck flask was then fitted with an addition funnel charged with bromine (5.70 mL, 111 mmol) in acetic acid (29.7 mL). The bromine solution was added over 30 min and the solution turned into a viscous and yellow mixture. After bromine addition was complete, the reaction mixture was allowed to warm to ambient temperature and stirred at that temperature for 16 h. Water (30 mL) was added to the reaction mixture and it was heated to 85° C. for 20 min before the solids were filtered and washed with water and methanol to give 5-fluorothiazolo[5,4-b]pyridin-2-amine (4.18 g, 24.71 mmol, 69.2% yield) as a yellow solid.

Workup

  1. customThe flask 3-neck flask was then fitted with an addition funnel
  2. temperaturewas heated to 85° C. for 20 min before the solids
  3. filtrationwere filtered
  4. washwashed with water and methanol

Sources & evidence

ORD record
ord-2b5e2c48c6314f21823de175afda05ac
Source dataset
uspto-grants-2012_10
Patent number
US08278320B2

Reaction notes

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