Pyrrolidine → HCID 59438405, compound

HRID 2177513Notes

Reaction equation

C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2)CCCCC1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].[NH:34]1[CH2:38][CH2:37][CH2:36][CH2:35]1.[CH3:39][O:40][C:41](=[O:53])[C:42]1[CH:47]=[CH:46][C:45]([C:48]([F:51])([F:50])[F:49])=[CH:44][C:43]=1Br>C1(C)C=CC=CC=1.ClCCl.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:39][O:40][C:41](=[O:53])[C:42]1[CH:43]=[CH:44][C:45]([C:48]([F:49])([F:51])[F:50])=[CH:46][C:47]=1[N:34]1[CH2:38][CH2:37][CH2:36][CH2:35]1

Participants

Conditions

Temperature: 80 °C

Procedure

To 30 mg (0.0318 mmol) Pd2 dba3, 37.9 mg (0.106 mmol) 2-(dicyclohexyl-phosphino)biphenyl and 315 mg (1.484 mmol) potassium phosphate tribasic under argon at room temperature, was added a solution of 105.2 ul (1.272 mmol) pyrrolidine in 5.5 ml toluene dry, followed by 300 mg (1.06 mmol) 2-bromo-4-trifluoromethyl-benzoic acid methyl ester (CAS: 328-89-2). The reaction mixture was heated at 80° C. overnight. The mixture was cooled to room temperature and diluted with dichloromethane. The suspension was filtered. The filtrate was concentrated in vacuo. The residue was purified on silica (Eluent: heptane/ethyl acetate 0 to 10%) to provide 88 mg (30.4%) of the title compound as an orange oil. MS (m/e): 274.3 (MH+).

Workup

customdry
temperatureThe mixture was cooled to room temperature
filtrationThe suspension was filtered
concentrationThe filtrate was concentrated in vacuo
customThe residue was purified on silica (Eluent: heptane/ethyl acetate 0 to 10%)

Sources & evidence

ORD record: ord-16cc00e23cd04fc2989771c569c9664d
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09067911B2

Reaction notes

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