Ethyl Acetate → N-(5-Bromo-3-phenoxypyridin-2-yl)thiazolo[5,4-b]pyridin-2-amine

HRID 1806100Notes

Reaction equation

HRID 1806100 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[CH:13]=[C:14]([O:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:15]([NH2:18])=[N:16][CH:17]=1.C(OCC)(=O)C>CN(C=O)C>[Br:11][C:12]1[CH:13]=[C:14]([O:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:15]([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:16][CH:17]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 128680882-Chloro-3-isothiocyanatopyridineHCID 459261405-Bromo-3-phenoxypyridin-2-amine

Product 1

HCID 57742902N-(5-Bromo-3-phenoxypyridin-2-yl)thiazolo[5,4-b]pyridin-2-amineYield 77.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

Heated a mixture of 2-chloro-3-isothiocyanatopyridine (0.257 g, 1.51 mmol) and 5-bromo-3-phenoxypyridin-2-amine (0.400 g, 1.51 mmol) in DMF (4 mL) at 80° C. for 3 hours. Heated at 120° C. overnight. Cooled, partitioned between 2N NaOH and ethyl acetate. Washed the organic layer twice with water, brine, dried, and concentrated. Subjected the residue to Biotage, eluting with 3:1 hexane:ethyl acetate to afford the title compound (0.465 g, 77.2% yield) as a white powder. 1H NMR (d6-DMSO) δ 7.15 (d, 2H), 7.23 (t, 1H), 7.40-7.50 (m, 4H), 7.92 (s, 1H), 8.34 (s, 1H), 8.37 (d, 1H), 11.63 (bs, 1H).

Workup

  1. temperatureHeated
  2. temperatureCooled
  3. custompartitioned between 2N NaOH and ethyl acetate
  4. washWashed the organic layer twice with water, brine
  5. customdried
  6. concentrationconcentrated
  7. washeluting with 3:1 hexane

Sources & evidence

ORD record
ord-a8e74f781d684a518577658ca291e6ad
Source dataset
uspto-grants-2013_01
Patent number
US08354540B2

Reaction notes

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