Dimethylformamide → HCID 69670779, compound

HRID 1191672Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([O:9][CH3:10])=[CH:4][C:3]=1[CH2:11][CH:12](O)[CH:13]([CH3:16])[CH2:14][CH3:15].C(=O)([O-])[O-].[K+].[K+].BrC1C(C)=CC(C)=CC=1C.CN(C)C=O>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[Cl:8][C:6]1[CH:7]=[C:2]2[C:3]([CH:11]=[C:12]([CH:13]([CH3:16])[CH2:14][CH3:15])[NH:1]2)=[CH:4][C:5]=1[O:9][CH3:10]

Participants

Conditions

Temperature: 160 °C

Procedure

A mixture of 1-(2-amino-4-chloro-5-methoxyphenyl)-3-methylpentan-2-ol (602 mg), tetrakis(triphenylphosphine)palladium (0) (135 mg), potassium carbonate (646 mg), 2-bromomesitylene (0.420 mL) and N,N-dimethylformamide (11.7 mL) was stirred at 160° C. for one hour under microwave irradiation. The reaction mixture was allowed to cool to ambient temperature. Water was added to the reaction mixture and this resulting mixture was extracted with ethyl acetate. The organic layer was washed with saturated saline, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane) to obtain the title compound (514 mg).

Workup

temperatureto cool to ambient temperature
extractionthis resulting mixture was extracted with ethyl acetate
washThe organic layer was washed with saturated saline
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane)

Sources & evidence

ORD record: ord-104e9aaa8fe846078490ac4f57996a64
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08680120B2

Reaction notes

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