Sodium Carbonate → Methyl 3-{3-[3-({[(2,2,2-trifluoro ethyl)amino]carbonyl}amino)phenyl]imidazo[1,2-b]pyridazin-7-yl}benzoate

HRID 407078Notes

Reaction equation

HRID 407078 reaction equation
I[C:2]1[N:6]2[N:7]=[CH:8][C:9]([C:11]3[CH:12]=[C:13]([CH:18]=[CH:19][CH:20]=3)[C:14]([O:16][CH3:17])=[O:15])=[CH:10][C:5]2=[N:4][CH:3]=1.CC1(C)C(C)(C)OB([C:29]2[CH:30]=[C:31]([NH:35][C:36]([NH:38][CH2:39][C:40]([F:43])([F:42])[F:41])=[O:37])[CH:32]=[CH:33][CH:34]=2)O1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.O.Cl[Pd](Cl)(P(C(C)(C)C)(C(C)(C)C)C1C=CC(N(C)C)=CC=1)P(C1C=CC(N(C)C)=CC=1)(C(C)(C)C)C(C)(C)C>[F:41][C:40]([F:42])([F:43])[CH2:39][NH:38][C:36]([NH:35][C:31]1[CH:32]=[C:33]([C:2]2[N:6]3[N:7]=[CH:8][C:9]([C:11]4[CH:12]=[C:13]([CH:18]=[CH:19][CH:20]=4)[C:14]([O:16][CH3:17])=[O:15])=[CH:10][C:5]3=[N:4][CH:3]=2)[CH:34]=[CH:29][CH:30]=1)=[O:37]

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 574976911-[3-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-3-(2,2,2-trifluoro-ethyl)-ureaHCID 67980176Methyl 3-(3-iodoimidazo[1,2-b]pyridazin-7-yl)benzoate

Product 1

HCID 67980357Methyl 3-{3-[3-({[(2,2,2-trifluoro ethyl)amino]carbonyl}amino)phenyl]imidazo[1,2-b]pyridazin-7-yl}benzoateYield 59.9%

Reagents, catalysts & solvents 3

HCID 178482906HCID 178482906, compoundCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

Dichloro(bis{di-tert-butyl[4-(dimethylamino)phenyl]phosphoranyl})palladium (6.7 mg, 0.0095 mmol) was added to a mixture of methyl 3-(3-iodoimidazo[1,2-b]pyridazin-7-yl)benzoate (0.12 g, 0.32 mmol), N-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-N′-(2,2,2-trifluoroethyl)urea (140 mg, 0.41 mmol) and sodium carbonate (67 mg, 0.63 mmol) in 1,4-dioxane (3 mL) and water (0.3 mL) and then the reaction vessel was evacuated under reduced pressure and refilled with nitrogen 3 times. The reaction was stirred at 100° C. overnight. To this mixture was added aqueous AcCN and then filtered, washed with aqueous AcCN, dried to provide the product (0.09 g). LCMS (M+H)+: m/z=470.1

Workup

  1. customthe reaction vessel was evacuated under reduced pressure
  2. additionrefilled with nitrogen 3 times
  3. additionTo this mixture was added aqueous AcCN
  4. filtrationfiltered
  5. washwashed with aqueous AcCN
  6. customdried

Sources & evidence

ORD record
ord-0a820e40330e4daf99594e8bfee9854c
Source dataset
uspto-grants-2014_06
Patent number
US08754114B2

Reaction notes

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