Toluene → 2-(2,4-Difluorophenylamino)-8-(2-morpholin-4-yl-ethoxy)-10,11-dihydrodibenzo[a,d]cyclohepten-5-one

HRID 473462Notes

Reaction equation

HRID 473462 reaction equation
ClC1C=CC2[C:11](=O)[C:10]3[CH:13]=[CH:14][CH:15]=[C:16]([O:17][CH2:18][CH2:19][N:20]4[CH2:25][CH2:24][O:23][CH2:22][CH2:21]4)[C:9]=3CCC=2C=1.[F:27][C:28]1[CH:34]=[C:33]([F:35])[CH:32]=[CH:31][C:29]=1[NH2:30].P.[O:37]([C:39](C)(C)C)[Na].[C:43]1([CH3:49])[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1>C(O)(C)(C)C.CC([O-])=O.CC([O-])=O.[Pd+2]>[F:27][C:28]1[CH:34]=[C:33]([F:35])[CH:32]=[CH:31][C:29]=1[NH:30][C:45]1[CH:46]=[CH:47][C:48]2[C:39](=[O:37])[C:13]3[CH:14]=[CH:15][C:16]([O:17][CH2:18][CH2:19][N:20]4[CH2:21][CH2:22][O:23][CH2:24][CH2:25]4)=[CH:9][C:10]=3[CH2:11][CH2:49][C:43]=2[CH:44]=1

Participants

8

Reactant 5

HCID 1140TolueneHCID 97092,4-DifluoroanilineHCID 24404PhosphineHCID 673608188-Chloro-1-(2-morpholin-4-yl-ethoxy)-10,11-dihydrodibenzo[a,d]cyclohepten-5-oneHCID 178418730sodium 2-methylpropan-2-olate

Product 1

HCID 452806382-(2,4-Difluorophenylamino)-8-(2-morpholin-4-yl-ethoxy)-10,11-dihydrodibenzo[a,d]cyclohepten-5-one

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6386tert-ButanolSolvent

Procedure

For the synthesis of the title compound, 0.45 g (0.0013 mol) of 8-chloro-1-(2-morpholin-4-yl-ethoxy)-10,11-dihydrodibenzo[a,d]cyclohepten-5-one, 0.20 g (0.0015 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.

Sources & evidence

ORD record
ord-55e9d154bfba4d238955151ebf20c629
Source dataset
uspto-grants-2014_01
Patent number
US08633312B2

Reaction notes

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