Water → 3-(2-Amino-3-(2-phenyl-pyridin-4-yl)imidazo[1,2-b]pyridazin-7-yl]-N-methyl-benzamide

HRID 1097312Notes

Reaction equation

HRID 1097312 reaction equation
[NH2:1][C:2]1[N:3]=[C:4]2[CH:9]=[C:8]([C:10]3[CH:11]=[C:12]([CH:17]=[CH:18][CH:19]=3)[C:13]([NH:15][CH3:16])=[O:14])[CH:7]=[N:6][N:5]2[C:20]=1[C:21]1[CH:26]=[CH:25][N:24]=[C:23](Cl)[CH:22]=1.[C:28]1(B(O)O)[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.O.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[NH2:1][C:2]1[N:3]=[C:4]2[CH:9]=[C:8]([C:10]3[CH:11]=[C:12]([CH:17]=[CH:18][CH:19]=3)[C:13]([NH:15][CH3:16])=[O:14])[CH:7]=[N:6][N:5]2[C:20]=1[C:21]1[CH:26]=[CH:25][N:24]=[C:23]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:22]=1

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 594435023-[2-Amino-3-(2-chloro-4-pyridinyl)imidazo[1,2-b]pyridazin-7-yl]-N-methylbenzamide

Product 1

HCID 251747803-(2-Amino-3-(2-phenyl-pyridin-4-yl)imidazo[1,2-b]pyridazin-7-yl]-N-methyl-benzamide

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

3-[2-Amino-3-(2-Chloro-pyridin-4-yl)-imidazo-[1,2-b]-pyridazin-7-yl]-N-methyl benzamide (1 eq, 0.146 mmol, 79 mg) and phenyl boronic acid (1.5 eq, 0.219 mmol, 27.5 mg) are dissolved in DME (1.5 ml) and water (0.4 ml) and Na2CO3 (3 eq, 0.438 mmol, 46.4 mg) are added. PdCl2(PPh3)2 (0.05 eq, 0.008 mmol, 5.12 mg) is then added and the reaction mixture is heated using microwave radiation at 120° C. for 15 min. At the completion of this time the solvent is removed in vacuo and the reaction mixture is purified by flash column chromatography eluting with 9:1 DCM/MeOH to yield 3-(2-Amino-3-(2-phenyl-pyridin-4-yl)imidazo [1,2-b]pyridazin-7-yl]-N-methyl-benzamide as a yellow solid; [M+H]+=421

Workup

  1. temperaturethe reaction mixture is heated
  2. customat 120° C.
  3. customfor 15 min
  4. customAt the completion of this time the solvent is removed in vacuo
  5. customthe reaction mixture is purified by flash column chromatography
  6. washeluting with 9:1 DCM/MeOH

Sources & evidence

ORD record
ord-9fbc1249a4ae415d966e274d18469200
Source dataset
uspto-grants-2012_03
Patent number
US08143253B2

Reaction notes

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