2,4-Difluoroaniline → HCID 45280642, compound

HRID 473472Notes

Reaction equation

HRID 473472 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][CH2:18][C@H:19]4[CH2:23][O:22][C:21]([CH3:25])([CH3:24])[O:20]4)[C:9]=3[CH2:8][CH2:7][C:6]=2[CH:26]=1.[F:27][C:28]1[CH:34]=[C:33]([F:35])[CH:32]=[CH:31][C:29]=1[NH2:30].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:27][C:28]1[CH:34]=[C:33]([F:35])[CH:32]=[CH:31][C:29]=1[NH:30][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][CH2:18][C@H:19]4[CH2:23][O:22][C:21]([CH3:25])([CH3:24])[O:20]4)[C:9]=3[CH2:8][CH2:7][C:6]=2[CH:26]=1

Participants

8

Reactant 4

HCID 97092,4-DifluoroanilineHCID 24404PhosphineHCID 67361716HCID 67361716, compoundHCID 178418730sodium 2-methylpropan-2-olate

Product 1

HCID 45280642HCID 45280642, compoundYield 37%

Reagents, catalysts & solvents 3

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

Procedure

For the synthesis of the title compound, 0.50 g (0.0013 mol) of (S)-8-chloro-1-(2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-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.

Sources & evidence

ORD record
ord-2500964f4a7e4c3989375415b548ffb6
Source dataset
uspto-grants-2014_01
Patent number
US08633312B2

Reaction notes

Loading…