2-Amino-3-bromopyridine → N-(3-bromopyridin-2-yl)thiazolo[5,4-b]pyridin-2-amine

HRID 335176Notes

Reaction equation

HRID 335176 reaction equation
Cl[C:2]1[C:7]([N:8]=[C:9]=[S:10])=[CH:6][CH:5]=[CH:4][N:3]=1.[Br:11][C:12]1[C:13]([NH2:18])=[N:14][CH:15]=[CH:16][CH:17]=1>CN(C=O)C>[Br:11][C:12]1[C:13]([NH:18][C:9]2[S:10][C:2]3[C:7]([N:8]=2)=[CH:6][CH:5]=[CH:4][N:3]=3)=[N:14][CH:15]=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 8177002-Amino-3-bromopyridineHCID 128680882-Chloro-3-isothiocyanatopyridine

Product 1

HCID 86631504N-(3-bromopyridin-2-yl)thiazolo[5,4-b]pyridin-2-amineYield 36.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

Heated a mixture of 2-chloro-3-isothiocyanatopyridine (0.986 g, 5.78 mmol) and 3-bromopyridin-2-amine (1.00 g, 5.78 mmol) in DMF (4 mL) at 80° C. for 3 hours. Heated at 120° C. overnight. Cooled, partitioned between ethyl acetate and water, washed with 2N NaOH, water, brine, dried, and concentrated. Crystallized from dichloromethane:hexanes (1:10, 110 mL) and filtered. The filtered material was further purified by dissolving in dichloromethane (10 mL), and subjecting to MPLC (Biotage) eluting with 3:2 hexane:ethyl acetate. The higher Rf component was concentrated to afford the title compound (0.654 g, 36.8% yield) as a white powder.

Workup

  1. temperatureHeated
  2. temperatureCooled
  3. custompartitioned between ethyl acetate and water
  4. washwashed with 2N NaOH, water, brine
  5. customdried
  6. concentrationconcentrated
  7. customCrystallized from dichloromethane:hexanes (1:10, 110 mL)
  8. filtrationfiltered
  9. customThe filtered material was further purified
  10. dissolutionby dissolving in dichloromethane (10 mL)
  11. washeluting with 3:2 hexane
  12. concentrationThe higher Rf component was concentrated

Sources & evidence

ORD record
ord-d8ba5a4008b345f88ccb1aeb9ed12d68
Source dataset
uspto-grants-2014_11
Patent number
US08883828B2

Reaction notes

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