1,2-Dimethoxyethane → 3-[(E)-2-(3,5-difluorophenyl)vinyl][1,4]benzodioxino[2,3-c]pyridazine

HRID 1503213Notes

Reaction equation

Cl[C:2]1[N:7]=[N:6][C:5]2[O:8][C:9]3[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=3[O:11][C:4]=2[CH:3]=1.COCCOC.C(=O)([O-])[O-].[Na+].[Na+].[F:28][C:29]1[CH:30]=[C:31](/[CH:36]=[CH:37]/B2OC(C)(C)C(C)(C)O2)[CH:32]=[C:33]([F:35])[CH:34]=1>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.O>[F:28][C:29]1[CH:30]=[C:31](/[CH:36]=[CH:37]/[C:2]2[N:7]=[N:6][C:5]3[O:8][C:9]4[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=4[O:11][C:4]=3[CH:3]=2)[CH:32]=[C:33]([F:35])[CH:34]=1

Participants

Conditions

Temperature: 100 °C

Procedure

Under an argon atmosphere, to 3-chloro[1,4]benzodioxino[2,3-c]pyridazine (500 mg) were added 1,2-dimethoxyethane (7.5 ml), 2M aqueous sodium carbonate solution (3.0 mL), 2-[(E)-2-(3,5-difluorophenyl)vinyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (720 mg) and tetrakis(triphenylphosphine)palladium (130 mg). The reaction mixture was stirred at 100° C. for 3 hr and cooled to room temperature. Water was added, and the obtained solid was collected by filtration and dried under reduced pressure to give 3-[(E)-2-(3,5-difluorophenyl)vinyl][1,4]benzodioxino[2,3-c]pyridazine (700 mg).

Workup

temperaturecooled to room temperature
filtrationthe obtained solid was collected by filtration
customdried under reduced pressure

Sources & evidence

ORD record: ord-684b39ef67014aa2b8e4380ea36e39b1
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09212147B2

Reaction notes

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