Sodium Carbonate → 4-Chloro-2-(3,5-dimethylphenyl)-7-fluoro-3-methylquinoline

HRID 1618534Notes

Reaction equation

Cl[C:2]1[C:11]([CH3:12])=[C:10]([Cl:13])[C:9]2[C:4](=[CH:5][C:6]([F:14])=[CH:7][CH:8]=2)[N:3]=1.[CH3:15][C:16]1[CH:17]=[C:18](B(O)O)[CH:19]=[C:20]([CH3:22])[CH:21]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.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>[Cl:13][C:10]1[C:9]2[C:4](=[CH:5][C:6]([F:14])=[CH:7][CH:8]=2)[N:3]=[C:2]([C:18]2[CH:19]=[C:20]([CH3:22])[CH:21]=[C:16]([CH3:15])[CH:17]=2)[C:11]=1[CH3:12]

Participants

Conditions

Temperature: 120 °C

Procedure

Prepared according to procedure F using 2,4-dichloro-7-fluoro-3-methylquinoline (500 mg, 2.173 mmol), 3,5-dimethylbenzeneboronic acid (326 mg, 2.173 mmol), sodium carbonate (1.15 g, 10.87 mmol) and Pd(PPh3)4 (251 mg, 0.217 mmol) in toluene/water (4 mL:1 mL) and heating in the microwave for 90 min at 120° C. After purification 4-chloro-2-(3,5-dimethylphenyl)-7-fluoro-3-methylquinoline was obtained as a white solid. Mass Spectrum (ESI) m/e=300 (M+1).

Workup

customPrepared
customAfter purification 4-chloro-2-(3,5-dimethylphenyl)-7-fluoro-3-methylquinoline
customwas obtained as a white solid

Sources & evidence

ORD record: ord-4cc10791e2a64c8f8c78111b607d5696
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765940B2

Reaction notes

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