Cesium carbonate → HCID 73297043, compound

HRID 592410Notes

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]#[N:31])=[N:28][CH:29]=1.C([O-])([O-])=O.[Cs+].[Cs+]>C1COCC1.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>[Cl:22][C:5]1[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)=[N:7][C:2]([NH:23][C:24]2[CH:29]=[N:28][C:27]([C:30]#[N:31])=[CH:26][CH:25]=2)=[N:3][CH:4]=1

Participants

Conditions

Temperature: 120 °C

Procedure

A solution of 1-(2-(2-(2,5-dichloropyrimidin-4-yl)ethyl)phenyl)cyclopropanecarboxamide A14 (0.300 g, 0.892 mmol) in THF (2.5 mL) containing 5-amino-2-pyridinecarbonitrile (0.213 g, 1.78 mmol), Cs2CO3 (0.872 g, 2.67 mmol), Xantphos (0.021 g, 0.036 mmol) and palladium (II) acetate (4 mg, 0.018 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, 12 g SiO2 Cartridge, 0-10% MeOH in DCM) to give the title compound 31 as a cream solid (0.262 g, 70%). LCMS-B: rt 7.13 min; m/z 419 [M+H]+.

Workup

custompurified by silica column chromatography (Combiflash Rf, 12 g SiO2 Cartridge, 0-10% MeOH in DCM)

Sources & evidence

ORD record: ord-45c02bffe475444da4351e57234209c1
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09238644B2

Reaction notes

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