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

HRID 473476Notes

Reaction equation

HRID 473476 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][CH:18]4[CH2:23][CH2:22][O:21][CH2:20][CH2:19]4)[C:9]=3[CH2:8][CH2:7][C:6]=2[CH:24]=1.[F:25][C:26]1[CH:32]=[C:31]([F:33])[CH:30]=[CH:29][C:27]=1[NH2:28].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:25][C:26]1[CH:32]=[C:31]([F:33])[CH:30]=[CH:29][C:27]=1[NH:28][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][CH:18]4[CH2:23][CH2:22][O:21][CH2:20][CH2:19]4)[C:9]=3[CH2:8][CH2:7][C:6]=2[CH:24]=1

Participants

8

Reactant 4

HCID 97092,4-DifluoroanilineHCID 24404PhosphineHCID 673624498-Chloro-1-(tetrahydropyran-4-yloxy)-10,11-dihydrodibenzo[a,d]cyclohepten-5-oneHCID 178418730sodium 2-methylpropan-2-olate

Product 1

HCID 452806948-(2,4-Difluorophenylamino)-1-(tetrahydropyran-4-yloxy)-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, 0.45 g (0.0013 mol) of 8-chloro-1-(tetrahydropyran-4-yloxy)-10,11-dihydrodibenzo[a,d]cyclohepten-5-one, 0.17 g (0.0013 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 70%/ethyl acetate 30%).

Sources & evidence

ORD record
ord-b6f91d8073c844b3b7b6848d32467abd
Source dataset
uspto-grants-2014_01
Patent number
US08633312B2

Reaction notes

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