Triethylamine → (R)-tert-butyl 1-(4-chloro-5,7-difluoro-3-methylquinolin-2-yl)pyrrolidine-2-carboxylate

HRID 1431702Notes

Reaction equation

Cl[C:2]1[C:11]([CH3:12])=[C:10]([Cl:13])[C:9]2[C:4](=[CH:5][C:6]([F:15])=[CH:7][C:8]=2[F:14])[N:3]=1.[NH:16]1[CH2:20][CH2:19][CH2:18][C@@H:17]1[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22].C(N(CC)CC)C>C(#N)C.O.C(O)(=O)C>[Cl:13][C:10]1[C:9]2[C:4](=[CH:5][C:6]([F:15])=[CH:7][C:8]=2[F:14])[N:3]=[C:2]([N:16]2[CH2:20][CH2:19][CH2:18][C@@H:17]2[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C:11]=1[CH3:12]

Participants

Conditions

Temperature: 140 °C

Procedure

The 2,4-dichloro-5,7-difluoro-3-methylquinoline (450 mg, 1.8 mmol), (R)-tert-butyl pyrrolidine-2-carboxylate (780 mg, 4.50 mmol) and triethylamine (0.63 mL, 4.5 mmol) were combined in acetonitrile (11 mL). The mixture was then heated in a microwave reactor at 140° C. for 90 min. The reaction mixture was then cond to dryness and diluted with water (35 mL) and acetic acid (3 mL) to acidify the solution. This mixture was extracted with EtOAc (1×100 mL) and DCM (1×100 mL). The combined organic layers were washed with water (50 mL) and brine (50 mL) and dried over magnesium sulfate. The filtrate was cond to obtain (R)-tert-butyl 1-(4-chloro-5,7-difluoro-3-methylquinolin-2-yl)pyrrolidine-2-carboxylate. Mass Spectrum (ESI) m/e=383.2 (M+1).

Workup

extractionThis mixture was extracted with EtOAc (1×100 mL) and DCM (1×100 mL)
washThe combined organic layers were washed with water (50 mL) and brine (50 mL)
dry with materialdried over magnesium sulfate

Sources & evidence

ORD record: ord-a4195245320643dba722447f9aead39e
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08940724B2

Reaction notes

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