Sodium Carbonate → 2'-Fluoro-5'-(7-isopropyl-7H-imidazo[4,5-c]pyridazin-4-yl)biphenyl-4-sulfonamide

HRID 1845988Notes

Reaction equation

Cl[C:2]1[C:3]2[N:10]=[CH:9][N:8]([CH:11]([CH3:13])[CH3:12])[C:4]=2[N:5]=[N:6][CH:7]=1.[F:14][C:15]1[CH:20]=[CH:19][C:18](B2OC(C)(C)C(C)(C)O2)=[CH:17][C:16]=1[C:30]1[CH:35]=[CH:34][C:33]([S:36]([NH2:39])(=[O:38])=[O:37])=[CH:32][CH:31]=1.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.O.C1C=CC(P([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C1C=CC(P([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.[Fe]>[F:14][C:15]1[CH:20]=[CH:19][C:18]([C:2]2[C:3]3[N:10]=[CH:9][N:8]([CH:11]([CH3:13])[CH3:12])[C:4]=3[N:5]=[N:6][CH:7]=2)=[CH:17][C:16]=1[C:30]1[CH:35]=[CH:34][C:33]([S:36]([NH2:39])(=[O:37])=[O:38])=[CH:32][CH:31]=1

Participants

Conditions

Temperature: 90 °C

Procedure

To 4-Chloro-7-isopropyl-7H-imidazo[4,5-c]pyridazine (Preparation 6, 50 mg, 0.254 mmoles) and 2′-fluoro-5′-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)biphenyl-4-sulfonamide (Preparation 2, 131 mg, 0.254 mmoles) in dioxane (2.5 mL) was added Na2CO3 (80 mg, 0.759 mmol) pre dissolved in water (0.5 mL) and [1,1-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (7.3 mg, 0.009 mmol). The reaction was degassed with nitrogen and heated under microwave irradiation at 90° C. for 15 minutes. After cooling, ethyl acetate and Na2SO4 were added and the mixture decanted and washed with ethyl acetate. Purification by silica gel column chromatography eluting with DCM: MeOH 1:0 to 9:1 yielded the title product in 50% yield, 57 mg.

Workup

customThe reaction was degassed with nitrogen
temperatureAfter cooling
additionethyl acetate and Na2SO4 were added
customthe mixture decanted
washwashed with ethyl acetate
customPurification by silica gel column chromatography
washeluting with DCM: MeOH 1:0 to 9:1

Sources & evidence

ORD record: ord-19451d24ac21407fb72bead5df319d90
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08952008B2

Reaction notes

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