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

HRID 1845988
Notes
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Reaction equation

HRID 1845988 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 867232144-chloro-7-isopropyl-7H-imidazo[4,5-c]pyridazineHCID 867232162'-Fluoro-5'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-4-sulfonamide

Product 1

HCID 867232152'-Fluoro-5'-(7-isopropyl-7H-imidazo[4,5-c]pyridazin-4-yl)biphenyl-4-sulfonamideYield 50%

Reagents, catalysts & solvents 3

HCID 178477754
HCID 178477754, compound
Catalyst
HCID 962WaterSolvent
HCID 312751,4-DioxaneSolvent

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

  1. customThe reaction was degassed with nitrogen
  2. temperatureAfter cooling
  3. additionethyl acetate and Na2SO4 were added
  4. customthe mixture decanted
  5. washwashed with ethyl acetate
  6. customPurification by silica gel column chromatography
  7. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes