[OH:1][C:2]([CH3:9])([CH3:8])[C:3]#[C:4]C(O)=O.CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.Br[C:63]1[CH:64]=[C:65]([CH:67]=[CH:68][CH:69]=1)[NH2:66]>C1COCC1.CC([O-])=O.CC([O-])=O.[Pd+2]>[NH2:66][C:65]1[CH:64]=[C:63]([C:4]#[C:3][C:2]([CH3:9])([OH:1])[CH3:8])[CH:69]=[CH:68][CH:67]=1In a 3-liter 4-neck flask provided with a mechanical stirrer there are introduced—in the order—64.0 g (0.50 mol, 1.0 eq.) of 4-hydroxy-4-methyl-2-pentinoic acid, 5.7 g of Pd(OAc)2 (5% mol), 24 g of XPhos (2-Dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl; 10% mol) and 378 g (1.5 mol, 3 eq. mol.) of TBAF (Tetra-n-butylammonium fluoride). The mixture is dissolved, under Argon atmosphere, in 2 L of distilled anhydrous THF. 55 ml of 3-Bromoaniline (d=1.585 g/mL, 0.5 mol, 1.0 eq. mol.) are added to this solution.
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