Cesium carbonate → HCID 73297044, compound

HRID 592411Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[C:16]2([C:19]([NH2:21])=[O:20])[CH2:18][CH2:17]2)[C:5]([Cl:22])=[CH:4][N:3]=1.[NH2:23][C:24]1[CH:25]=[CH:26][C:27]([C:30](=[O:32])[CH3:31])=[N:28][CH:29]=1.C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>[C:30]([C:27]1[N:28]=[CH:29][C:24]([NH:23][C:2]2[N:7]=[C:6]([CH2:8][CH2:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[C:16]3([C:19]([NH2:21])=[O:20])[CH2:18][CH2:17]3)[C:5]([Cl:22])=[CH:4][N:3]=2)=[CH:25][CH:26]=1)(=[O:32])[CH3:31]

Participants

Conditions

Temperature: 120 °C

Procedure

A solution of 1-(2-(2-(2,5-dichloropyrimidin-4-yl)ethyl)phenyl)cyclopropanecarboxamide A14 (0.200 g, 0.595 mmol) in 1,4-dioxane (2.0 mL) containing 1-(5-aminopyridin-2-yl)ethanone (0.121 g, 0.892 mmol), Cs2CO3 (0.581 g, 1.78 mmol), Xantphos (0.014 g, 0.024 mmol) and palladium (II) acetate (2.67 mg, 0.012 mmol) was heated under microwave irradiation for 30 minutes at 120° C. The reaction mixture was adsorbed onto silica gel and purified by silica column chromatography (Combiflash Rf, 4 g SiO2 Cartridge, 0-10% MeOH in DCM) to give title compound 32 as a light cream solid (0.183 g, 70%). LCMS-B: rt 6.98 min; m/z 437 [M+H]+.

Workup

custompurified by silica column chromatography (Combiflash Rf, 4 g SiO2 Cartridge, 0-10% MeOH in DCM)

Sources & evidence

ORD record: ord-e11d00a3a4e54f7083ce4caec130f1a5
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09238644B2

Reaction notes

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