Potassium Carbonate → HCID 86696383, compound

HRID 870680Notes

Reaction equation

HRID 870680 reaction equation
Br[C:2]1[N:6]2[N:7]=[C:8]([NH:11][CH2:12][CH2:13][CH2:14][CH3:15])[CH:9]=[CH:10][C:5]2=[N:4][CH:3]=1.B([C:19]1[CH:27]=[CH:26][C:22]([C:23]([OH:25])=[O:24])=[CH:21][CH:20]=1)(O)O.C(=O)([O-])[O-].[K+].[K+]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(#N)C.O>[CH2:12]([NH:11][C:8]1[CH:9]=[CH:10][C:5]2[N:6]([C:2]([C:19]3[CH:27]=[CH:26][C:22]([C:23]([OH:25])=[O:24])=[CH:21][CH:20]=3)=[CH:3][N:4]=2)[N:7]=1)[CH2:13][CH2:14][CH3:15]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 3121834-Carboxyphenylboronic AcidHCID 866963223-Bromo-6-(butylamino)imidazo[1,2-b]pyridazine

Product 1

HCID 86696383HCID 86696383, compoundYield 226.6%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 18373917Acetonitrile--water (1/1)Solvent

Conditions

Temperature
145 °C

Procedure

To the mixture of 3-bromo-N-butylimidazo[1,2-b]pyridazin-6-amine (340 mg, 1.26 mmol), 4-boronobenzoic acid (210 mg, 1.26 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (44 mg, 0.063 mmol) and potassium carbonate (261 mg, 1.89 mmol) was added 3:1 acetonitrile/water (3 mL). The resulting mixture was heated at 145° C. (microwave) for 800 s. The reaction was then filtered and concentrated to afford 4-(6-(butylamino)imidazo[1,2-b]pyridazin-3-yl)benzoic acid (886 mg, >100% yield) as a crude off-white solid: LRMS (ESI) m/e 311.2 [(M+H)+, calcd for C17H19N4O2 311.2].

Workup

  1. filtrationThe reaction was then filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-c88469973ca845369bdb86212189180a
Source dataset
uspto-grants-2015_03
Patent number
US08969565B2

Reaction notes

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