Sodium Carbonate → 6-Chloro-4-(4-methoxy-2-methylphenyl)-3-pyridazineamine

HRID 501002

Reaction equation

Br[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[N:4][C:3]=1[NH2:9].[CH3:10][O:11][C:12]1[CH:17]=[CH:16][C:15](B(O)O)=[C:14]([CH3:21])[CH:13]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C(O)C>[Cl:8][C:6]1[N:5]=[N:4][C:3]([NH2:9])=[C:2]([C:15]2[CH:16]=[CH:17][C:12]([O:11][CH3:10])=[CH:13][C:14]=2[CH3:21])[CH:7]=1

Participants

Conditions

Temperature: 100 °C

Procedure

4-Bromo-6-chloro-3-pyridazineamine (12 g) and 4-methoxy-2-methylphenylboronic acid (10.5 g) were dissolved in a mixed solvent of toluene (240 mL) and ethanol (45 mL), then tetrakistriphenylphosphine palladium complex (6.7 g) and a 2M aqueous sodium carbonate solution (24 mL) were added thereto, and the mixture was heated under stirring at 100° C. for 12 hours. After completion of the reaction, the solvent was evaporated. The residue was extracted with ethyl acetate, washed with water, and dried over anhydrous magnesium sulfate, and then the solvent was evaporated. The residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:4) to give the title compound (7.89 g) as brown crystals.

Workup

temperaturethe mixture was heated
customAfter completion of the reaction
customthe solvent was evaporated
extractionThe residue was extracted with ethyl acetate
washwashed with water
dry with materialdried over anhydrous magnesium sulfate
customthe solvent was evaporated
customThe residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:4)

Sources & evidence

ORD record: ord-6fa9ab8aece6499dba6053cbaea6e650
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07772249B2

Linked notes

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