Cesium carbonate → HCID 117823884, compound

HRID 59110Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][C:9]=1[N:10]1[CH:14]=[C:13]([CH3:15])[N:12]=[CH:11]1)[NH2:6].Cl[C:17]1[N:22]=[C:21]([O:23][CH2:24][C:25]([F:28])([F:27])[F:26])[C:20]([CH3:29])=[C:19]([CH2:30][O:31][CH2:32][C:33]([F:36])([F:35])[F:34])[N:18]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2)CCCCC1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:6][C:17]2[N:22]=[C:21]([O:23][CH2:24][C:25]([F:28])([F:26])[F:27])[C:20]([CH3:29])=[C:19]([CH2:30][O:31][CH2:32][C:33]([F:36])([F:34])[F:35])[N:18]=2)[CH:7]=[CH:8][C:9]=1[N:10]1[CH:14]=[C:13]([CH3:15])[N:12]=[CH:11]1

Participants

Conditions

Temperature: 120 °C

Procedure

3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)aniline (0.066 g, 0.32 mmol), 2-chloro-5-methyl-4-(2,2,2-trifluoroethoxy)-6-((2,2,2-trifluoroethoxy)methyl)pyrimidine (0.11 g, 0.32 mmol), palladium(II) acetate (11 mg, 0.05 mmol), 2-(dicyclohexylphosphino)biphenyl (0.017 g, 0.05 mmol) and cesium carbonate (0.212 g, 0.65 mmol) were mixed in dioxane (3 mL). The vial was capped, evacuated and flushed with nitrogen. The mixture was heated by microwave irradiation at 120° C. for 1.5 h. The mixture was filtered and the residue was purified by column chromatography on silica eluting with a gradient of methanol in DCM to give the title compound 135 mg (82%).

Workup

customThe vial was capped
customevacuated
customflushed with nitrogen
filtrationThe mixture was filtered
customthe residue was purified by column chromatography on silica eluting with a gradient of methanol in DCM

Sources & evidence

ORD record: ord-a9582943f32d4539ac8117f9ba8a6e29
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09439904B2

Reaction notes

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