2,4-Difluoroaniline → HCID 60167139, compound

HRID 473504Notes

Reaction equation

HRID 473504 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]2[C:11](=[O:12])[C:10]3[CH:13]=[CH:14][C:15]([O:17][CH2:18][CH2:19][CH2:20][O:21]C(=O)C)=[CH:16][C:9]=3[CH2:8][CH2:7][C:6]=2[CH:25]=1.[F:26][C:27]1[CH:33]=[C:32]([F:34])[CH:31]=[CH:30][C:28]=1[NH2:29].P>C1(C)C=CC=CC=1.C(O)(C)(C)C.CC([O-])=O.CC([O-])=O.[Pd+2]>[F:26][C:27]1[CH:33]=[C:32]([F:34])[CH:31]=[CH:30][C:28]=1[NH:29][C:2]1[CH:3]=[CH:4][C:5]2[C:11](=[O:12])[C:10]3[CH:13]=[CH:14][C:15]([O:17][CH2:18][CH2:19][CH2:20][OH:21])=[CH:16][C:9]=3[CH2:8][CH2:7][C:6]=2[CH:25]=1

Participants

7

Reactant 3

HCID 97092,4-DifluoroanilineHCID 24404PhosphineHCID 67498110HCID 67498110, compound

Product 1

HCID 60167139HCID 60167139, compoundYield 42%

Reagents, catalysts & solvents 3

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

Procedure

In accordance with general method O, 0.65 g (1.8 mmol) of acetic acid 3-(8-chloro-5-oxo-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-2-yloxy)-propyl ester, 0.25 g (1.9 mmol) of 2,4-difluoroaniline, 0.04 g of Pd(OAc)2, 0.17 g of phosphine ligand and 0.74 g (7.7 mmol) of Na—O-tert-butylate are reacted in 10 ml of toluene and 2 ml of tert-BuOH. Yield: 42%; m.p.: 154° C.

Sources & evidence

ORD record
ord-523d6c7ff4a545a1bfc2a0fb6f03f908
Source dataset
uspto-grants-2014_01
Patent number
US08633312B2

Reaction notes

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