Reaction #8357

Reaction equation

3-[4-(2-pyridin-2-yl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)-quinolin-7-ylsulfanyl]-propan-1-ol

toluene sulfonyl chloride

sodium bicarbonate

→

desired product

7-(3-Chloro-propylsulfanyl)-4-(2-pyridin-2-yl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)-quinoline

Solvents

pyridine

Conditions

Workup

1. 1
   Extractionthe resulting solution extracted with ethyl acetate
2. 2
   WashThe organic layer is washed with brine
3. 3
   Dryingdried (sodium sulfate)
4. 4
   Filtrationfiltered
5. 5
   Concentrationconcentrated in vacuo
6. 6
   OtherPurification of the residue on SiO2 (5% to 10% methanol in dichloromethane)

Procedure

To a solution of Preparation #21, 3-[4-(2-pyridin-2-yl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)-quinolin-7-ylsulfanyl]-propan-1-ol (25.0 mg, 0.062 mmol) in dry pyridine (0.1 mL) is added toluene sulfonyl chloride (60.0 mg, 0.31 mmol) and the resulting mixture stirred at room temperature for 72 h. Saturated sodium bicarbonate solution is added and the resulting solution extracted with ethyl acetate. The organic layer is washed with brine, dried (sodium sulfate), filtered, and concentrated in vacuo. Purification of the residue on SiO2 (5% to 10% methanol in dichloromethane) gives the desired product, 11.2 mg (43%). MS ES+ m/e 421.1 (M+1).

Source