Dichloromethane → 1-(5,7-Di-pyridin-3-yl-benzothiazol-2-yl)-3-ethyl-urea

HRID 1010635Notes

Reaction equation

HRID 1010635 reaction equation
Br[C:2]1[CH:3]=[C:4](Br)[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+].C(Cl)Cl>CN(C=O)C.O>[N:18]1[CH:23]=[CH:22][CH:21]=[C:20]([C:2]2[CH:3]=[C:4]([C:20]3[CH:19]=[N:18][CH:23]=[CH:22][CH:21]=3)[C:5]3[S:9][C:8]([NH:10][C:11]([NH:13][CH2:14][CH3:15])=[O:12])=[N:7][C:6]=3[CH:16]=2)[CH:19]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 62657Potassium Phosphate, TribasicHCID 27343783-Pyridinylboronic acidHCID 578135675,7-Dibromo-benzothiazol-2-yl-3-ethyl urea

Product 1

HCID 248642181-(5,7-Di-pyridin-3-yl-benzothiazol-2-yl)-3-ethyl-urea

Reagents, catalysts & solvents 1

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

Conditions

Temperature
120 °C

Procedure

To a solution of 1-(5,7-dibromo-benzothiazol-2-yl)-3-ethyl-urea (1.60 g, 0.40 mmol) in DMF-H2O (2:1, 48 mL) was added pyridine-3-boronic acid (0.51 g, 0.42 mmol) and K3PO4 (0.90 g, 0.42 mmol) under nitrogen atmosphere at room temperature. The reaction mixture was then degassed for 30 min followed by addition of [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) complex with CH2Cl2 (0.35 g, 0.042 mmol). The reaction mixture was then again degassed for 30 min and heated at 120° C. for 1 h under nitrogen atmosphere. DMF was distilled off, water was added into reaction mixture and extracted with ethyl acetate (×3). The combined organic layer was dried over anhydrous Na2SO4, and evaporated to dryness under reduced pressure. The compound was purified over silica (230-400 M) using ethyl acetate/hexane (gradient) to provide the desired compounds.

Workup

  1. customThe reaction mixture was then degassed for 30 min
  2. customThe reaction mixture was then again degassed for 30 min
  3. distillationDMF was distilled off
  4. additionwater was added into reaction mixture
  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 compound was purified over silica (230-400 M)

Sources & evidence

ORD record
ord-dd0804e345ac4f87aa24a7b4bc8bd46f
Source dataset
uspto-grants-2011_07
Patent number
US07977340B2

Reaction notes

Loading…