2-Fluoro-5-nitrophenylboronic acid, pinacol ester → 4-Chloro-7-fluoro-2-(2-fluoro-5-nitrophenyl)-3-methylquinoline

HRID 1431631Notes

Reaction equation

HRID 1431631 reaction equation
ClC1C(C)=C(Cl)C2C(=CC=CC=2F)N=1.Cl[C:16]1[C:25]([CH3:26])=[C:24]([Cl:27])[C:23]2[C:18](=[CH:19][C:20]([F:28])=[CH:21][CH:22]=2)[N:17]=1.[F:29][C:30]1[CH:35]=[CH:34][C:33]([N+:36]([O-:38])=[O:37])=[CH:32][C:31]=1B1OC(C)(C)C(C)(C)O1>>[Cl:27][C:24]1[C:23]2[C:18](=[CH:19][C:20]([F:28])=[CH:21][CH:22]=2)[N:17]=[C:16]([C:31]2[CH:32]=[C:33]([N+:36]([O-:38])=[O:37])[CH:34]=[CH:35][C:30]=2[F:29])[C:25]=1[CH3:26]

Participants

4

Reactant 3

HCID 38332972-Fluoro-5-nitrophenylboronic acid, pinacol esterHCID 596311082,4-Dichloro-7-fluoro-3-methylquinolineHCID 596315132,4-Dichloro-5-fluoro-3-methylquinoline

Product 1

HCID 596314484-Chloro-7-fluoro-2-(2-fluoro-5-nitrophenyl)-3-methylquinoline

Procedure

Essentially prepared according to Procedure F using a mixture of 2,4-dichloro-5-fluoro-3-methylquinoline and 2,4-dichloro-7-fluoro-3-methylquinoline (˜1:4 mixture) (690 mg, 3.00 mmol) and 2-(2-fluoro-5-nitrophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane to give 4-chloro-7-fluoro-2-(2-fluoro-5-nitrophenyl)-3-methylquinoline. Mass Spectrum (ESI) m/e=335.0 (M+1).

Workup

  1. customEssentially prepared

Sources & evidence

ORD record
ord-b22da20079f14bcaafc9743d57f82d4e
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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