Cesium carbonate → HCID 70571541, compound

HRID 2403588Notes

Reaction equation

[CH3:1][N:2]([CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([C:21]2[CH:22]=[N:23][C:24]([N:27]3[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]3)=[N:25][CH:26]=2)[CH:16]=1)[C:3](=[O:13])[CH2:4][NH:5][C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9].Br[C:34]1[CH:41]=[CH:40][C:37]([C:38]#[N:39])=[CH:36][N:35]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C1(C)C=CC=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]>[C:38]([C:37]1[CH:40]=[CH:41][C:34]([N:30]2[CH2:31][CH2:32][N:27]([C:24]3[N:25]=[CH:26][C:21]([C:17]4[CH:16]=[C:15]([CH:20]=[CH:19][CH:18]=4)[CH2:14][N:2]([CH3:1])[C:3](=[O:13])[CH2:4][NH:5][C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:9])[CH3:10])=[CH:22][N:23]=3)[CH2:28][CH2:29]2)=[N:35][CH:36]=1)#[N:39]

Participants

Conditions

Temperature: 100 °C

Procedure

Under an argon atmosphere, tert-butyl (2-{methyl[3-(2-piperazin-1-ylpyrimidin-5-yl)benzyl]amino}-2-oxoethyl)carbamate (200 mg) and 6-bromonicotinonitrile (124 mg) were dissolved in toluene (6 ml), and tris(dibenzylideneacetone)dipalladium (124 mg), 1,1′-binaphthalene-2,2′-diylbis(diphenylphosphine) (169 mg), and cesium carbonate (222 mg) were added thereto, followed by stirring at 100° C. for 6 hours. The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (0% to 7% MeOH/CHCl3) to obtain tert-butyl {2-[(3-{2-[4-(5-cyanopyridin-2-yl)piperazin-1-yl]pyrimidin-5-yl}benzyl)(methyl)amino]-2-oxoethyl}carbamate (122 mg).

Workup

customThe solvent was evaporated under reduced pressure
customthe obtained residue was purified by silica gel column chromatography (0% to 7% MeOH/CHCl3)

Sources & evidence

ORD record: ord-61efe7a429f44e07aed9d58cd84ead59
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08802679B2

Reaction notes

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