Cesium carbonate → HCID 117824132, compound

HRID 59089Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([C:8]([O:10][CH2:11][CH3:12])=[CH2:9])[CH:5]=[C:4]([CH2:13][O:14][CH2:15][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].C(=O)([O-])[O-].[Cs+].[Cs+].C1(C2C=CC=CC=2)C=CC=CC=1P(C1CCCCC1)C1CCCCC1>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:11]([O:10][C:8]([C:6]1[CH:5]=[C:4]([CH2:13][O:14][CH2:15][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

A mixture of 2-chloro-4-(1-ethoxyvinyl)-6-((3,3,3-trifluoropropoxy)methyl)pyrimidine (89 mg, 0.29 mmol), 3-methoxy-4-(4-methyl-1H-imidazol-1-yl)aniline (58 mg, 0.29 mmol), cesium carbonate (187 mg, 0.57 mmol), palladium (II) acetate (10 mg, 0.04 mmol) and (2-biphenylyl)dicyclohexylphosphine (15 mg, 0.04 mmol) in dioxane (3 mL) was heated at 120° C. under argon for 90 minutes in microwave reactor. The mixture was passed through a short silica plug which was eluted with EtOAc. The residue was purified by preparative HPLC to give the title compound as a dry film 93 mg (68%).

Workup

washwas eluted with EtOAc
customThe residue was purified by preparative HPLC

Sources & evidence

ORD record: ord-837b90405a8b4ab0beba18b406b5c0e0
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09439904B2

Reaction notes

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