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Cesium fluoride → 5-(2-Chlorophenylthio)-6-(4-methylthiazol-2-ylamino)pyridin-3-ol

HRID 1806027
Notes
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Reaction equation

HRID 1806027 reaction equation
Br[C:2]1[CH:3]=[C:4]([S:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[Cl:22])[C:5]([NH:8][C:9]2[S:10][CH:11]=[C:12]([CH3:14])[N:13]=2)=[N:6][CH:7]=1.CC1(C)C(C)(C)OB(B2OC(C)(C)C(C)(C)O2)[O:25]1.C1(P(C2CCCC2)C2CCCC2)CCCC1.[F-].[Cs+]>C(#N)C.CC([O-])=O.CC([O-])=O.[Pd+2]>[Cl:22][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[S:15][C:4]1[CH:3]=[C:2]([OH:25])[CH:7]=[N:6][C:5]=1[NH:8][C:9]1[S:10][CH:11]=[C:12]([CH3:14])[N:13]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 25953Cesium fluorideHCID 2733548Bis(pinacolato)diboraneHCID 4463278Phosphine, tricyclopentyl-HCID 24764526N-(5-bromo-3-(2-chlorophenylthio)pyridin-2-yl)-4-methylthiazol-2-amine

Product 1

HCID 247645195-(2-Chlorophenylthio)-6-(4-methylthiazol-2-ylamino)pyridin-3-ol

Reagents, catalysts & solvents 2

HCID 167845
palladium(II) acetate
Catalyst
HCID 6342AcetonitrileSolvent

Conditions

Temperature
90 °C

Procedure

A degassed mixture of N-(5-bromo-3-(2-chlorophenylthio)pyridin-2-yl)-4-methylthiazol-2-amine (1.10 g, 2.66 mmol), 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi(1,3,2-dioxaborolane) (1.35 g, 5.32 mmol), Pd(OAc)2 (60 mg, 0.27 mmol), tricyclopentylphosphine (93 mg. 0.40 mmol) and cesium fluoride (3.64 g, 23.9 mmol) in acetonitrile is heated at 90° C. for 5 hours. The reaction mixture is cooled and partitioned between ether and water. The crude product is dissolved in THF. N-morpholine N-oxide (1.40 g, 12.0 mmol) is added and the reaction mixture is heated at reflux for 12 hours. The reaction mixture is cooled and partitioned between ether and water. The organic layer is washed with water and brine, dried and concentrated. The residue is purified by silica gel chromatography, eluting with 10-20% EtOAc in hexanes to afford the title compound.

Workup

  1. temperatureThe reaction mixture is cooled
  2. custompartitioned between ether and water
  3. dissolutionThe crude product is dissolved in THF
  4. temperaturethe reaction mixture is heated
  5. temperatureat reflux for 12 hours
  6. temperatureThe reaction mixture is cooled
  7. custompartitioned between ether and water
  8. washThe organic layer is washed with water and brine
  9. customdried
  10. concentrationconcentrated
  11. customThe residue is purified by silica gel chromatography
  12. washeluting with 10-20% EtOAc in hexanes

Sources & evidence

ORD record
ord-4be61383afca4b9dbda5ac66457c36b4
Source dataset
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08354540B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes