Toluene → HCID 45280584, compound

HRID 473458Notes

Reaction equation

HRID 473458 reaction equation
Cl[C:2]1[CH:17]=[CH:16][C:5]2[C:6](=O)C3C=CC=CC=3CC[C:4]=2[C:3]=1[O:18][CH2:19][C@H:20]1[CH2:24][O:23][C:22]([CH3:26])([CH3:25])[O:21]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:16]3[CH:17]=[CH:2][C:3]([O:18][CH2:19][C@H:20]4[CH2:24][O:23][C:22]([CH3:25])([CH3:26])[O:21]4)=[CH:4][C:5]=3[CH2:6][CH2:49][C:43]=2[CH:44]=1

Participants

8

Reactant 5

HCID 1140TolueneHCID 97092,4-DifluoroanilineHCID 24404PhosphineHCID 67360668HCID 67360668, compoundHCID 178418730sodium 2-methylpropan-2-olate

Product 1

HCID 45280584HCID 45280584, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6386tert-ButanolSolvent

Procedure

For the synthesis of the title compound, 0.81 g (0.0022 mol) of (S)-2-chloro-1-(2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-10,11-dihydrodibenzo[a,d]cyclohepten-5-one, 0.25 g (0.0019 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 80%/ethyl acetate 20%).

Sources & evidence

ORD record
ord-c8110f1ad98948a2bf853b78699d6942
Source dataset
uspto-grants-2014_01
Patent number
US08633312B2

Reaction notes

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