Cesium carbonate → HCID 57932909, compound

HRID 1432627Notes

Reaction equation

HRID 1432627 reaction equation
[CH2:1]([CH:3]([C:6]1[C:7]2[N:8]([CH:13]=[C:14]([CH3:16])[N:15]=2)[N:9]=[C:10]([CH3:12])[CH:11]=1)[CH2:4][CH3:5])[CH3:2].Br[C:18]1[S:22][C:21]([C:23]2[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=2)=[CH:20][C:19]=1[Cl:29].C([O-])([O-])=O.[Cs+].[Cs+].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Cl:29][C:19]1[CH:20]=[C:21]([C:23]2[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=2)[S:22][C:18]=1[C:13]1[N:8]2[N:9]=[C:10]([CH3:12])[CH:11]=[C:6]([CH:3]([CH2:4][CH3:5])[CH2:1][CH3:2])[C:7]2=[N:15][C:14]=1[CH3:16]

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 11776TriphenylphosphineHCID 688412672,6-Dimethyl-8-(pentan-3-yl)imidazo[1,2-b]pyridazineHCID 68843597HCID 68843597, compound

Product 1

HCID 57932909HCID 57932909, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Procedure

Using a procedure similar to Example 85 Method B Step C, from 8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazine (0.50 g, 2.30 mmol), 3-(5-bromo-4-chloro-thiophen-2-yl)-pyridine) (0.76 g, 2.76 mmol), Cs2CO3 (1.57 g, 4.83 mmol), PPh3 (0.11 g, 0.44 mmol) and Pd2(dba)3 (0.10 g, 0.11 mmol). The residue is purified by ISCO column chromatography (15%-30% EtOAc/hexane gradient) furnish the title compound (0.35 g, 0.85 mmol, 37%). Spectrum identical to Method A.

Workup

  1. customThe residue is purified by ISCO column chromatography (15%-30% EtOAc/hexane gradient)

Sources & evidence

ORD record
ord-bfbdd335ebca4072a329bdbcbf8dd2aa
Source dataset
uspto-grants-2009_11
Patent number
US07612067B2

Reaction notes

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