Cesium carbonate → HCID 10178987, compound

HRID 1392988Notes

Reaction equation

HRID 1392988 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[N:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:11]3=[N:10][CH:9]=2)[CH:5]=[CH:4][N:3]=1.Br[C:18]1[CH:23]=[CH:22][C:21]([C:24]([C:26]2[S:27][CH:28]=[CH:29][N:30]=2)=[O:25])=[CH:20][CH:19]=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].[Pd]>[S:27]1[CH:28]=[CH:29][N:30]=[C:26]1[C:24]([C:21]1[CH:20]=[CH:19][C:18]([NH:1][C:2]2[N:7]=[C:6]([C:8]3[N:12]4[CH:13]=[CH:14][CH:15]=[CH:16][C:11]4=[N:10][CH:9]=3)[CH:5]=[CH:4][N:3]=2)=[CH:23][CH:22]=1)=[O:25]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 11777777HCID 11777777, compoundHCID 691978644-(Imidazo[1,2-a]pyridin-3-yl)pyrimidin-2-amine

Product 1

HCID 10178987HCID 10178987, compoundYield 45%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Procedure

The title compound was prepared from 2-amino-4-(imidazo-[1,2-a]pyridin-3-yl)pyrimidine and (4-bromophenyl)(1,3-thiazol-2-yl)methanone following the general method of Example 1 using cesium carbonate as the base and tris(dibenzylideneacetone)dipalladium (0) as the palladium source. The crude product was purified by column chromatography on silica gel using chloroform/ethanol, 95:5, as the eluent affording 0.126 g (45% yield) of the title compound as a yellow solid: mp (decomp.) 234-235° C.; MS (TSP) m/z 399 (M+1);

Workup

  1. customThe crude product was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-0ee02bea9fa74b55ac20ebfc0e0edc84
Source dataset
uspto-grants-2008_03
Patent number
US07345050B2

Reaction notes

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