Potassium Carbonate → N-(2-(4-fluorophenyl)-2-methylpropyl)-6-vinylpyridazin-3-amine

HRID 869144Notes

Reaction equation

Cl[C:2]1[N:7]=[N:6][C:5]([NH:8][CH2:9][C:10]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)([CH3:12])[CH3:11])=[CH:4][CH:3]=1.[CH:20](B1OB(C=C)OB(C=C)O1)=[CH2:21].C(=O)([O-])[O-].[K+].[K+].O1CCOCC1>O.C(OCC)(=O)C>[F:19][C:16]1[CH:17]=[CH:18][C:13]([C:10]([CH3:12])([CH3:11])[CH2:9][NH:8][C:5]2[N:6]=[N:7][C:2]([CH:20]=[CH2:21])=[CH:3][CH:4]=2)=[CH:14][CH:15]=1

Participants

Conditions

Temperature: 140 °C

Procedure

To a 5 mL microwave reaction vial was added 6-chloro-N-(2-(4-fluorophenyl)-2-methylpropyl)pyridazin-3-amine (123 mg, 441 μmol, 1.0 equiv), 2,4,6-trivinyl-1,3,5,2,4,6-trioxatriborinane (159 mg, 661 μmol, 1.5 equiv), Cl2Pd(dppf) (54 mg, 66 μmol, 0.15 equiv), potassium carbonate (182 mg, 1.32 mmol, 3 equiv), and dioxane (21 mL). The reaction was heated in a microwave reactor at 140° C. for 12 min and then diluted with water (20 mL) and ethyl acetate (50 mL). After transferring to a separatory funnel and shaking, the organic layer was separated from the aqueous layer and then washed with brine (1×20 mL). The organic layer was then dried over Na2SO4, filtered, and concentrated to give a crude solid that was purified by silica gel column chromatography (20-50% EtOAc/hexanes) to give 50 mg (46%) of N-(2-(4-fluorophenyl)-2-methylpropyl)-6-vinylpyridazin-3-amine as a white solid.

Workup

customTo a 5 mL microwave reaction
customAfter transferring to a separatory funnel
customthe organic layer was separated from the aqueous layer
washwashed with brine (1×20 mL)
dry with materialThe organic layer was then dried over Na2SO4
filtrationfiltered
concentrationconcentrated
customto give a crude solid that
customwas purified by silica gel column chromatography (20-50% EtOAc/hexanes)

Sources & evidence

ORD record: ord-8c8b5cd2843c4affbc3f08ec58cadfca
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08969346B2

Reaction notes

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