Cesium carbonate → HCID 117824346, compound

HRID 59111Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([C:8]([O:10][CH2:11][CH3:12])=[CH2:9])[C:5]([CH3:13])=[C:4]([CH2:14][O:15][CH2:16][C:17]([F:20])([F:19])[F:18])[N:3]=1.[CH3:21][O:22][C:23]1[CH:24]=[C:25]([CH:27]=[CH:28][C:29]=1[N:30]1[CH:34]=[C:33]([CH3:35])[N:32]=[CH:31]1)[NH2:26].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>[CH2:11]([O:10][C:8]([C:6]1[C:5]([CH3:13])=[C:4]([CH2:14][O:15][CH2:16][C:17]([F:20])([F:19])[F:18])[N:3]=[C:2]([NH:26][C:25]2[CH:27]=[CH:28][C:29]([N:30]3[CH:34]=[C:33]([CH3:35])[N:32]=[CH:31]3)=[C:23]([O:22][CH3:21])[CH:24]=2)[N:7]=1)=[CH2:9])[CH3:12]

Participants

Conditions

Temperature: 120 °C

Procedure

2-Chloro-4-(1-ethoxyvinyl)-5-methyl-6-((2,2,2-trifluoroethoxy)methyl)pyrimidine (70 mg, 0.23 mmol), 3-methoxy-4-(4-methyl-1H-imidazol-1-yl)aniline (46 mg, 0.23 mmol), palladium(II) acetate (8 mg, 0.03 mmol), 2-(dicyclohexylphosphino)biphenyl (12 mg, 0.03 mmol) and cesium carbonate (147 mg, 0.45 mmol) were mixed in dioxane (4 mL). The vial was capped, evacuated and flushed with nitrogen. The reaction mixture was heated by microwave irradiation at 120° C. for 1.5 h. The mixture was filtered through a pad of silica and the silica was washed by 5% of MeOH in DCM. The solvents were evaporated and the residue was purified by preparative HPLC to give the title compound 52 mg (48%).

Workup

customThe vial was capped
customevacuated
customflushed with nitrogen
filtrationThe mixture was filtered through a pad of silica
washthe silica was washed by 5% of MeOH in DCM
customThe solvents were evaporated
customthe residue was purified by preparative HPLC

Sources & evidence

ORD record: ord-23ca24a48eea440c9bc841f64cc17ad8
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09439904B2

Reaction notes

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