Hydrochloric Acid → HCID 67284726, compound

HRID 1618546Notes

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].[Br:24][C:25]1[CH:26]=[C:27]2[NH:33][CH2:32][C:31]([CH3:35])([CH3:34])[C:28]2=[N:29][CH:30]=1.Cl.O1CCOCC1>CN1C(=O)CCC1>[Br:24][C:25]1[CH:26]=[C:27]2[N:33]([C:2]3[C:11]4[C:6](=[CH:7][C:8]([F:12])=[CH:9][CH:10]=4)[N:5]=[C:4]([C:13]4[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=4[S:19]([CH3:22])(=[O:21])=[O:20])[C:3]=3[CH3:23])[CH2:32][C:31]([CH3:35])([CH3:34])[C:28]2=[N:29][CH:30]=1

Participants

Conditions

Temperature: 150 °C

Procedure

Prepared according to procedure L using 4-chloro-7-fluoro-3-methyl-2-(2-(methylsulfonyl)phenyl)quinoline (242 mg, 0.69 mmol) (described herein), 6-bromo-3,3-dimethyl-2,3-dihydro-1H-pyrrolo[3,2-b]pyridine (157 mg, 0.69 mmol) (described herein), 4.0 M hydrochloric acid in 1,4-dioxane (0.17 mL, 0.69 mmol), and NMP (1.2 mL). The reaction mixture was stirred and heated in a microwave at 150° C. for 120 min. Chromatography afforded 4-(6-bromo-3,3-dimethyl-2,3-dihydro-1H-pyrrolo[3,2-b]pyridin-1-yl)-7-fluoro-3-methyl-2-(2-(methylsulfonyl)-phenyl)quinoline as a dark oil. Mass Spectrum (ESI) m/e=541 (M+1).

Workup

customPrepared

Sources & evidence

ORD record: ord-2f7e1e9bae1c474c8f6e3843fd93504c
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765940B2

Reaction notes

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