Hydrochloric Acid → 7-Fluoro-4-(6-iodo-3,3-dimethylindolin-1-yl)-3-methyl-2-(2-(methylsulfonyl)phenyl)quinoline

HRID 1618544Notes

Reaction equation

Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([F:12])=[CH:9][CH:10]=2)[N:5]=[C:4]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[S:19]([CH3:22])(=[O:21])=[O:20])[C:3]=1[CH3:23].[I:24][C:25]1[CH:33]=[C:32]2[C:28]([C:29]([CH3:35])([CH3:34])[CH2:30][NH:31]2)=[CH:27][CH:26]=1.Cl>CN1C(=O)CCC1>[F:12][C:8]1[CH:7]=[C:6]2[C:11]([C:2]([N:31]3[C:32]4[C:28](=[CH:27][CH:26]=[C:25]([I:24])[CH:33]=4)[C:29]([CH3:35])([CH3:34])[CH2:30]3)=[C:3]([CH3:23])[C:4]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[S:19]([CH3:22])(=[O:21])=[O:20])=[N:5]2)=[CH:10][CH:9]=1

Participants

Conditions

Temperature: 150 °C

Procedure

Prepared according to procedure L using 4-chloro-7-fluoro-3-methyl-2-(2-(methylsulfonyl)phenyl)quinoline (102 mg, 0.29 mmol) (described herein), 6-iodo-3,3-dimethylindoline (80 mg, 0.29 mmol) (described herein), hydrochloric acid (70 μL, 0.29 mmol), and NMP (0.490 mL). The reaction mixture was heated in a microwave at 150° C. for 150 min. Purification afforded 7-fluoro-4-(6-iodo-3,3-dimethylindolin-1-yl)-3-methyl-2-(2-(methylsulfonyl)phenyl)quinoline as a yellow solid. Mass Spectrum (ESI) m/e=587 (M+1).

Workup

customPrepared
customPurification

Sources & evidence

ORD record: ord-2fcf5c62094f45e8b90971a4e115b994
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765940B2

Reaction notes

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