Water → HCID 23160371, compound

HRID 1876021Notes

Reaction equation

HRID 1876021 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 3-neck flask containing a mechanically stirred suspension of potassium rhodanate (27.7 g, 285 mmol) in acetic acid (89 mL) at 0° C. The 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 yellow mixture. After bromine addition was complete, the reaction mixture was allowed to warm to ambient temperature and stirred for 16 h. Water (30 mL) was added and the mixture 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. additioncontaining
  2. customThe flask was then fitted with an addition funnel
  3. temperaturethe mixture was heated to 85° C. for 20 min before the solids
  4. filtrationwere filtered
  5. washwashed with water and methanol

Sources & evidence

ORD record
ord-fd0ecfc59be0468d9168d1d2225987a2
Source dataset
uspto-grants-2012_11
Patent number
US08309577B2

Reaction notes

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