Potassium Carbonate → 5-(3-Chlorophenyl)-6-p-tolylpyridazin-3(2H)-one

HRID 1430607Notes

Reaction equation

HRID 1430607 reaction equation
Br[C:2]1[C:7]([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=2)=[N:6][NH:5][C:4](=[O:15])[CH:3]=1.[Cl:16][C:17]1[CH:18]=[C:19](B(O)O)[CH:20]=[CH:21][CH:22]=1.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:16][C:17]1[CH:22]=[C:21]([C:2]2[C:7]([C:8]3[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=3)=[N:6][NH:5][C:4](=[O:15])[CH:3]=2)[CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 2734323(3-Chlorophenyl)boronic acidHCID 674344105-bromo-6-p-tolylpyridazin-3(2H)-one

Product 1

HCID 674347465-(3-Chlorophenyl)-6-p-tolylpyridazin-3(2H)-oneYield 57.1%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
130 °C

Procedure

In a 10 mL heavy-walled sealed tube, a mixture of 5-bromo-6-p-tolylpyridazin-3(2H)-one (0.05 g, 0.189 mmol), 3-chlorophenylboronic acid (0.029 g, 0.189 mmol), Pd(Ph3P)4 (10.90 mg, 9.43 μmol) and K2CO3 (0.283 mL, 0.566 mmol) in dioxane (2 mL) was heated under microwave irradiation at 130° C. for 2 h. The reaction was purified by preparative HPLC to give the title compound (0.032 g). LCMS m/z=297.1 [M+H]+.

Workup

  1. customThe reaction was purified by preparative HPLC

Sources & evidence

ORD record
ord-87804414d21b4f81b9ac372f29c6d7cb
Source dataset
uspto-grants-2015_01
Patent number
US08940891B2

Reaction notes

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