2-Bromo-5-fluoroanisole → 8-Nitro-3-(4-fluoro-2-methoxyphenylamino)-6H-dibenzo[b,e]oxepin-11-one

HRID 473492Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[C:11](=[O:12])[C:10]3[CH:13]=[CH:14][C:15]([N+:17]([O-:19])=[O:18])=[CH:16][C:9]=3[CH2:8][O:7][C:6]=2[CH:20]=1.Br[C:22]1[CH:27]=[CH:26][C:25]([F:28])=[CH:24][C:23]=1[O:29][CH3:30].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1.CC([O-])(C)C.[K+]>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2].CC(O)(C)C>[N+:17]([C:15]1[CH:14]=[CH:13][C:10]2[C:11](=[O:12])[C:5]3[CH:4]=[CH:3][C:2]([NH:1][C:22]4[CH:27]=[CH:26][C:25]([F:28])=[CH:24][C:23]=4[O:29][CH3:30])=[CH:20][C:6]=3[O:7][CH2:8][C:9]=2[CH:16]=1)([O-:19])=[O:18]

Participants

Conditions

Temperature: 100 °C

Procedure

In accordance with general method Z, 0.70 g (2.60 mmol) of (6), 0.55 g (2.68 mmol) of 2-bromo-5-fluoroanisole, 2 spatula tips of Pd(OAc)2, 0.10 g of 2-(dicyclohexylphosphino)-2′,4′,6′-triisopropylbiphenyl (phosphine ligand), 0.50 g of KOt-Bu, 2.0 ml of t-BuOH are weighed out and dissolved in 10 ml of toluene (anhydrous). The mixture is refluxed at 100° C. under an argon atmosphere for 4 h. The crude product is purified by chromatography over silica gel with MC/EtOH (98/2). Yield: 0.07 g (0.01%); melting point: 222.3° C.

Workup

customThe crude product is purified by chromatography over silica gel with MC/EtOH (98/2)

Sources & evidence

ORD record: ord-5a3ff32a02374f7d9d6c0bacb5b0db6b
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08633312B2

Reaction notes

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