4-Bromobenzophenone → HCID 10157263, compound

HRID 1392983Notes

Reaction equation

HRID 1392983 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:31]=[CH:30][C:21]([C:22]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[O:23])=[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]>[C:22]([C:24]1[CH:29]=[CH:28][C:27]([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:26][CH:25]=1)(=[O:23])[C:21]1[CH:30]=[CH:31][CH:18]=[CH:19][CH:20]=1

Participants

6

Reactant 3

HCID 70304-BromobenzophenoneHCID 10796Cesium carbonateHCID 691978644-(Imidazo[1,2-a]pyridin-3-yl)pyrimidin-2-amine

Product 1

HCID 10157263HCID 10157263, compoundYield 58%

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-bromobenzophenone 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 0.14 g (58% yield) of the title compound as a yellow solid: mp (decomp.) 249-255° C.; MS (TSP) m/z 392 (M+1 ), 1H NMR (400 MHz, DMSO-d6) δ 10.38 (s, 1 H), 10.35 (d, J=6.8 Hz, 1 H), 9.03 (s, 1 H), 8.67 (d, J=5.4 Hz, 1 H), 8.01 (d, J=8.7 Hz, 2 H), 7.98 (m, 1 H), 7.87 (m, 1 H), 7.83 (d, J=8.7 Hz, 2 H), 7.76 (d, J=7.0 Hz; 2 H), 7.69 (m, 1 H), 7.59 (m, 3 H), 7.47 (m, 1 H).

Workup

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

Sources & evidence

ORD record
ord-39e481e6b4174de1b273f63094f8c727
Source dataset
uspto-grants-2008_03
Patent number
US07345050B2

Reaction notes

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