Cesium carbonate → HCID 86682737, compound

HRID 1755386Notes

Reaction equation

HRID 1755386 reaction equation
Br[C:2]1[C:3]2[N:4]([CH:9]=[CH:10][N:11]=2)[N:5]=[C:6]([Cl:8])[CH:7]=1.[C:12]([CH:16]1[CH2:20][CH2:19][N:18]([C:21]2[N:26]=[C:25]([NH2:27])[CH:24]=[CH:23][CH:22]=2)[CH2:17]1)([CH3:15])([CH3:14])[CH3:13].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.C([O-])([O-])=O.[Cs+].[Cs+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O1CCOCC1>[C:12]([CH:16]1[CH2:20][CH2:19][N:18]([C:21]2[N:26]=[C:25]([NH:27][C:2]3[C:3]4[N:4]([CH:9]=[CH:10][N:11]=4)[N:5]=[C:6]([Cl:8])[CH:7]=3)[CH:24]=[CH:23][CH:22]=2)[CH2:17]1)([CH3:15])([CH3:13])[CH3:14]

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 468352698-Bromo-6-chloroimidazo(1,2-b)pyridazineHCID 86682736HCID 86682736, compound

Product 1

HCID 86682737HCID 86682737, compoundYield 43.7%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 8-bromo-6-chloroimidazo[1,2-b]pyridazine (573 mg, 2.47 mmol), 6-(3-tert-butylpyrrolidin-1-yl)pyridin-2-amine (540 mg, 2.47 mmol), Pd2(dba)3 (142 mg, 0.25 mmol), BINAP (307 mg, 0.50 mmol), Cs2CO3 (2.4 g, 7.41 mmol) and dioxane (20 mL) was heated to reflux with stirring for 15 h under N2. The solvent was removed in vacuo and the resulting mixture was purified by chromatography (silica gel, 200-300 mesh, dichloromethane:MeOH=50:1) to give N-(6-(3-tert-butylpyrrolidin-1-yl)pyridin-2-yl)-6-chloroimidazo[1,2-b]pyridazin-8-amine (400 mg, crude) as a brown oil. LC-MS: [M+H]+, 371.1, tR=2.23 min.

Workup

  1. temperaturewas heated
  2. temperatureto reflux
  3. customThe solvent was removed in vacuo
  4. customthe resulting mixture was purified by chromatography (silica gel, 200-300 mesh, dichloromethane:MeOH=50:1)

Sources & evidence

ORD record
ord-cdc012ac554543f7af7cc5bd9077e1a7
Source dataset
uspto-grants-2015_10
Patent number
US09169259B2

Reaction notes

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