Hydrochloric Acid → 2-(2,5-Difluorophenyl)-7-fluoro-4-(6-iodo-3,3-dimethylindolin-1-yl)-3-methylquinoline

HRID 1618563Notes

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]=[C:17]([F:19])[CH:16]=[CH:15][C:14]=2[F:20])[C:3]=1[CH3:21].[I:22][C:23]1[CH:31]=[C:30]2[C:26]([C:27]([CH3:33])([CH3:32])[CH2:28][NH:29]2)=[CH:25][CH:24]=1.Cl.O1CCOCC1>CN1C(=O)CCC1>[F:20][C:14]1[CH:15]=[CH:16][C:17]([F:19])=[CH:18][C:13]=1[C:4]1[C:3]([CH3:21])=[C:2]([N:29]2[C:30]3[C:26](=[CH:25][CH:24]=[C:23]([I:22])[CH:31]=3)[C:27]([CH3:33])([CH3:32])[CH2:28]2)[C:11]2[C:6](=[CH:7][C:8]([F:12])=[CH:9][CH:10]=2)[N:5]=1

Participants

Conditions

Temperature: 150 °C

Procedure

Prepared according to procedure L using 4-chloro-2-(2,5-difluorophenyl)-7-fluoro-3-methylquinoline (150 mg, 0.49 mmol) (described herein), 6-iodo-3,3-dimethylindoline (160 mg, 0.59 mmol) (described herein), and 4.0 hydrochloric acid in 1,4-dioxane (120 μL, 0.49 mmol) in NMP (810 μL). The reaction mixture was stirred and heated at 150° C. for 3 h. Purification afforded 2-(2,5-difluorophenyl)-7-fluoro-4-(6-iodo-3,3-dimethylindolin-1-yl)-3-methylquinoline as a yellow solid. Mass Spectrum (ESI) m/e=545 (M+1).

Workup

customPrepared
customPurification

Sources & evidence

ORD record: ord-2e304b6694ab4534b4bdbd8f3616415e
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765940B2

Reaction notes

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