2,4-Difluoroaniline → 2-(2,4-Difluorophenylamino)-8-methoxy-10,11-dihydrodibenzo[a,d]cyclo-hepten-5-one

HRID 473506Notes

Reaction equation

HRID 473506 reaction equation
Cl[C:2]1[CH:19]=[CH:18][C:5]2[C:6](=[O:17])[C:7]3[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][C:8]=3[CH2:9][CH2:10][C:4]=2[CH:3]=1.[F:20][C:21]1[CH:27]=[C:26]([F:28])[CH:25]=[CH:24][C:22]=1[NH2:23].P>C1(C)C=CC=CC=1.C(O)(C)(C)C.CC([O-])=O.CC([O-])=O.[Pd+2]>[F:20][C:21]1[CH:27]=[C:26]([F:28])[CH:25]=[CH:24][C:22]=1[NH:23][C:2]1[CH:19]=[CH:18][C:5]2[C:6](=[O:17])[C:7]3[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][C:8]=3[CH2:9][CH2:10][C:4]=2[CH:3]=1

Participants

7

Reactant 3

HCID 97092,4-DifluoroanilineHCID 24404PhosphineHCID 67361741HCID 67361741, compound

Product 1

HCID 601671372-(2,4-Difluorophenylamino)-8-methoxy-10,11-dihydrodibenzo[a,d]cyclo-hepten-5-oneYield 66%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolventHCID 6386tert-ButanolSolvent

Procedure

In accordance with general method O, 0.52 g (1.9 mmol) of 2-chloro-8-methoxy-10,11-dihydrodibenzo[a,d]cyclohepten-5-one, 0.30 g (2.3 mmol) of 2,4-difluoroaniline, 0.04 g of Pd(OAc)2, 0.16 g of phosphine ligand and 0.86 g (8.9 mmol) of Na—O-tert-butylate are reacted in 10 ml of toluene and 2 ml of tert-BuOH. Purification is carried out by column chromatography (flash; SiO2; hexane 90%/ethyl acetate 10%). Yield: 66%; m.p.: 157° C.

Workup

  1. customPurification

Sources & evidence

ORD record
ord-9a6050c769b04dba8fa169f5bec1d48b
Source dataset
uspto-grants-2014_01
Patent number
US08633312B2

Reaction notes

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