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

HRID 1618512Notes

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][N:14]=2)[C:3]=1[CH3:19].[I:20][C:21]1[CH:29]=[C:28]2[C:24]([C:25]([CH3:31])([CH3:30])[CH2:26][NH:27]2)=[CH:23][CH:22]=1.Cl.O1CCOCC1>CN1C(=O)CCC1>[F:12][C:8]1[CH:7]=[C:6]2[C:11]([C:2]([N:27]3[C:28]4[C:24](=[CH:23][CH:22]=[C:21]([I:20])[CH:29]=4)[C:25]([CH3:31])([CH3:30])[CH2:26]3)=[C:3]([CH3:19])[C:4]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=3)=[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-(pyridin-2-yl)quinoline (250 mg, 0.92 mmol), 6-iodo-3,3-dimethylindoline (250 mg, 0.92 mmol) and 4.0M solution of HCl in 1,4-dioxane (0.22 mL, 0.92 mmol) in NMP (1.0 mL) and heating at 150° C. for 3 h in the microwave. After purification 7-fluoro-4-(6-iodo-3,3-dimethylindolin-1-yl)-3-methyl-2-(pyridin-2-yl)quinoline was obtained as a foam. Mass Spectrum (ESI) m/e=510 (M+1).

Workup

customPrepared
customAfter purification 7-fluoro-4-(6-iodo-3,3-dimethylindolin-1-yl)-3-methyl-2-(pyridin-2-yl)quinoline
customwas obtained as a foam

Sources & evidence

ORD record: ord-19e8ff0fde9646c4a42a77b896b27f63
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765940B2

Reaction notes

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