Ethyl Acetate → HCID 60209565, compound

HRID 2246221Notes

Reaction equation

HRID 2246221 reaction equation
Cl[C:2]1[N:7]=[N:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])=[O:15])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[F:23][C:24]([F:35])([F:34])[C:25]1[CH:26]=[C:27](B(O)O)[CH:28]=[CH:29][CH:30]=1.C(OCC)(=O)C>C1CCCCC1>[F:23][C:24]([F:35])([F:34])[C:25]1[CH:30]=[C:29]([C:2]2[N:7]=[N:6][C:5]([N:8]3[CH2:13][CH2:12][N:11]([C:14]([O:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])=[O:15])[CH2:10][CH2:9]3)=[CH:4][CH:3]=2)[CH:28]=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 27343883-(Trifluoromethyl)phenylboronic acidHCID 60209564HCID 60209564, compound

Product 1

HCID 60209565HCID 60209565, compoundYield 43.7%

Reagents, catalysts & solvents 1

HCID 8078CyclohexaneSolvent

Procedure

The process is performed according to the procedure described in Example 1 (step 1.3.). Starting with 1.15 g (3.50 mmol) of 2-(ethyloxy)-2-oxoethyl 4-(6-chloro-3-pyridazinyl)-1-piperazinecarboxylate, obtained in step 10.1., 1.99 g (10.49 mmol) of 3-(trifluoromethyl)phenyl-boronic acid, 2.97 g (13.99 mmol) of hydrated potassium phosphate and 0.40 g (0.35 mmol) of tetrakis(triphenyl-phosphine)palladium, and after chromatography on silica gel, eluting with a 35/65 and then 45/55 mixture of ethyl acetate and cyclohexane, 0.67 g of pure product is obtained in the form of a solid.

Workup

  1. customobtained in step 10.1

Sources & evidence

ORD record
ord-32271bbcee794f789ec7af87e850a128
Source dataset
uspto-grants-2010_03
Patent number
US07687503B2

Reaction notes

Loading…