Potassium Phosphate, Tribasic → HCID 44199211, compound

HRID 1969106Notes

Reaction equation

HRID 1969106 reaction equation
Cl[C:2]1[CH:3]=[C:4]([NH2:11])[C:5]2[N:6]([CH:8]=[CH:9][N:10]=2)[N:7]=1.[C:12]([C:16]1[CH:40]=[CH:39][C:19]([C:20]([NH:22][C:23]2[CH:28]=[CH:27][CH:26]=[C:25](B3OC(C)(C)C(C)(C)O3)[C:24]=2[CH3:38])=[O:21])=[CH:18][CH:17]=1)([CH3:15])([CH3:14])[CH3:13].P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.C(O)CCC>[NH2:11][C:4]1[C:5]2[N:6]([CH:8]=[CH:9][N:10]=2)[N:7]=[C:2]([C:25]2[C:24]([CH3:38])=[C:23]([NH:22][C:20](=[O:21])[C:19]3[CH:18]=[CH:17][C:16]([C:12]([CH3:13])([CH3:14])[CH3:15])=[CH:40][CH:39]=3)[CH:28]=[CH:27][CH:26]=2)[CH:3]=1

Participants

8

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 57786732HCID 57786732, compoundHCID 587289934-(tert-Butyl)-N-(2-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)benzamide

Product 1

HCID 44199211HCID 44199211, compoundYield 23%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 2631-ButanolSolventHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 6-chloro-imidazo[1,2-b]pyridazin-8-ylamine (0.048 g, 0.29 mmol), 4-tert-butyl-N-[2-methyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-benzamide (0.169 g, 0.444 mmol), potassium phosphate (0.120 g, 0.567 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (0.024 g, 0.058 mmol), palladium acetate (0.007 g, 0.03 mmol), 0.5 mL of n-butanol and 0.2 mL of water in a sealed tube was stirred at 100° C. for 2 d. The resulting cloudy orange mixture was partitioned between 5 mL of ethyl acetate and 5 mL of water, and the aqueous layer was extracted with 5 mL of ethyl acetate. The combined organic layers were dried over MgSO4, filtered and concentrated to an orange oil. Column chromatography (60->100% EtOAc/hexanes) afforded 0.026 g (23%) of N-[3-(8-amino-imidazo[1,2-b]pyridazin-6-yl)-2-methyl-phenyl]-4-tert-butyl-benzamide as a yellow solid.

Workup

  1. customThe resulting cloudy orange mixture was partitioned between 5 mL of ethyl acetate and 5 mL of water
  2. extractionthe aqueous layer was extracted with 5 mL of ethyl acetate
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated to an orange oil

Sources & evidence

ORD record
ord-ce0617db2f6c4688b77176ed594bb7fd
Source dataset
uspto-grants-2013_04
Patent number
US08426441B2

Reaction notes

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