Potassium Phosphate, Tribasic → HCID 24864394, compound

HRID 1941932Notes

Reaction equation

HRID 1941932 reaction equation
[I:1][C:2]1[CH:3]=[C:4](I)[C:5]2[S:9][C:8]([NH:10][C:11]([NH:13][CH2:14][CH3:15])=[O:12])=[N:7][C:6]=2[CH:16]=1.[N:18]1[CH:23]=[CH:22][CH:21]=[C:20](B(O)O)[CH:19]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>CN(C=O)C.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>[CH2:14]([NH:13][C:11]([NH:10][C:8]1[S:9][C:5]2[C:4]([C:20]3[CH:19]=[N:18][CH:23]=[CH:22][CH:21]=3)=[CH:3][C:2]([I:1])=[CH:16][C:6]=2[N:7]=1)=[O:12])[CH3:15]

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 27343783-Pyridinylboronic acidHCID 57813756HCID 57813756, compound

Product 1

HCID 24864394HCID 24864394, compound

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 1-(5,7-diiodo-benzothiazol-2-yl)-3-ethyl-urea (0.20 g, 0.42 mmol) in DMF (5 mL) was added pyridine 3-boronic acid (0.076 g, 0.63 mmol) and K3PO4 (0.133 g, 0.63 mmol) under nitrogen atmosphere at room temperature. The reaction mixture was degassed for half an hour followed by the addition of bis(triphenylphosphine)palladium(II) dichloride (0.0044 g, 0.063 mmol). The reaction mixture was again degassed for half an hour and then heated at 120° C. for 1 h under nitrogen atmosphere. DMF was distilled off, added water and extracted with ethyl acetate (×3). The combined organic layer was dried over anhydrous Na2SO4, and evaporated to dryness under reduced pressure. The residue was purified by chromatography on silica (230-400 M) using DCM/Methanol (99:1) to provide 1-Ethyl-3-(5-iodo-7-pyridin-3-yl-benzothiazol-2-yl)-urea as an off white solid (0.025 g, 14%) and DCM/Methanol (98:2) to provide 1-Ethyl-3-(7-iodo-5-pyridin-3-yl-benzothiazol-2-yl)-urea as an off white solid (0.025 g, 14%).

Workup

  1. customThe reaction mixture was degassed for half an hour
  2. customThe reaction mixture was again degassed for half an hour
  3. distillationDMF was distilled off
  4. additionadded water
  5. extractionextracted with ethyl acetate (×3)
  6. dry with materialThe combined organic layer was dried over anhydrous Na2SO4
  7. customevaporated to dryness under reduced pressure
  8. customThe residue was purified by chromatography on silica (230-400 M)

Sources & evidence

ORD record
ord-0a5329fd4f5742a2af37ec693ad7adae
Source dataset
uspto-grants-2013_03
Patent number
US08389516B2

Reaction notes

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