Potassium Phosphate, Tribasic → HCID 24864398, compound

HRID 1941939Notes

Reaction equation

HRID 1941939 reaction equation
Br[C:2]1[C:10]2[S:9][C:8]([NH:11][C:12]([NH:14][CH2:15][CH3:16])=[O:13])=[N:7][C:6]=2[CH:5]=[C:4]([N:17]2[CH:21]=[CH:20][CH:19]=[N:18]2)[CH:3]=1.[N:22]1[CH:27]=[CH:26][CH:25]=[C:24](B(O)O)[CH:23]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>CN(C=O)C.O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:15]([NH:14][C:12]([NH:11][C:8]1[S:9][C:10]2[C:2]([C:24]3[CH:23]=[N:22][CH:27]=[CH:26][CH:25]=3)=[CH:3][C:4]([N:17]3[CH:21]=[CH:20][CH:19]=[N:18]3)=[CH:5][C:6]=2[N:7]=1)=[O:13])[CH3:16]

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 27343783-Pyridinylboronic acidHCID 57813627HCID 57813627, compound

Product 1

HCID 24864398HCID 24864398, compoundYield 24.5%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 21962138N,N-Dimethylformamide--water (1/1)Solvent

Conditions

Temperature
120 °C

Procedure

To a solution of 1-(7-bromo-5-pyrazol-1-yl-benzothiazol-2-yl)-3-ethyl-urea (0.27 g, 0.74 mmol) in DMF: H2O (2:1, 15 mL) was added 3-pyridyl boronic acid (0.11 g, 0.88 mmol) and K3PO4 (0.17 g, 0.81 mmol) under nitrogen atmosphere at room temperature. The reaction mixture was then degassed for half an hour followed by the addition of bis(triphenylphosphine)palladium(II) dichloride (0.077 g, 0.11 mmol). The reaction mixture was then again degassed for half an hour and heated at 120° C. for 2 h under nitrogen atmosphere. After the completion of the reaction (TLC monitoring), DMF was distilled off; water was added to the reaction mixture and extracted with ethyl acetate. The combined organic layers were dried over anhydrous Na2SO4, and evaporated to dryness under reduced pressure. The crude residue was purified over silica gel (230-400 M) using EtOAc-Hexane (70:30) to provide the title compound (0.066 g, 22%).

Workup

  1. customThe reaction mixture was then degassed for half an hour
  2. customThe reaction mixture was then again degassed for half an hour
  3. customAfter the completion of the reaction (TLC monitoring), DMF
  4. distillationwas distilled off
  5. additionwater was added to the reaction mixture
  6. extractionextracted with ethyl acetate
  7. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  8. customevaporated to dryness under reduced pressure
  9. customThe crude residue was purified over silica gel (230-400 M)

Sources & evidence

ORD record
ord-5046c8cdead24f3fb777ed4ba7640c50
Source dataset
uspto-grants-2013_03
Patent number
US08389516B2

Reaction notes

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