2,4-Difluoroaniline → 8-(2,4-Difluorophenylamino)-1-methoxy-10,11-dihydrodibenzo[a,d]cyclohepten-5-one

HRID 473469Notes

Reaction equation

HRID 473469 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]2[C:11](=[O:12])[C:10]3[CH:13]=[CH:14][CH:15]=[C:16]([O:17][CH3:18])[C:9]=3[CH2:8][CH2:7][C:6]=2[CH:19]=1.[F:20][C:21]1[CH:27]=[C:26]([F:28])[CH:25]=[CH:24][C:22]=1[NH2:23].P.O(C(C)(C)C)[Na]>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:3]=[CH:4][C:5]2[C:11](=[O:12])[C:10]3[CH:13]=[CH:14][CH:15]=[C:16]([O:17][CH3:18])[C:9]=3[CH2:8][CH2:7][C:6]=2[CH:19]=1

Participants

8

Reactant 4

HCID 97092,4-DifluoroanilineHCID 24404PhosphineHCID 67360944HCID 67360944, compoundHCID 178418730sodium 2-methylpropan-2-olate

Product 1

HCID 452806408-(2,4-Difluorophenylamino)-1-methoxy-10,11-dihydrodibenzo[a,d]cyclohepten-5-one

Reagents, catalysts & solvents 3

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

Procedure

For the synthesis of the title compound, 0.54 g (0.0020 mol) of 8-chloro-1-methoxy-10,11-dihydrodibenzo[a,d]cyclohepten-5-one, 0.26 g (0.0020 mol) of 2,4-difluoroaniline, 2 spatula tips of Pd(OAc)2, 0.14 g of phosphine ligand and 0.70 g (0.0073 mol) of NaOtert-Bu in 10 ml of toluene and 2 ml of tert-BuOH are reacted by method O. Purification is carried out by column chromatography (flash; SiO2; hexane 90%/ethyl acetate 10%). C22H17F2NO2 (Mr=365.38)

Sources & evidence

ORD record
ord-07ef2bc75eae4f0f9a163b0ca4f956b5
Source dataset
uspto-grants-2014_01
Patent number
US08633312B2

Reaction notes

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