[C:1]1(B(O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:14][O:13][C:12]=1[CH:21]=[O:22].C(#N)C.C(O)=O>C1COCC1.O.CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.[Pd]>[C:1]1([C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH2:14][O:13][C:12]=2[CH:21]=[O:22])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1
X-phos Pd G2 (116 mg, 0,147 mmol) and phenylboronic acid (538 mg, 4.41 mmol) were sealed in a closed vessel equipped with a magnetic bar and oxygen removed by Ar/vacuum cycle. A degassed solution of 4-chloro-1H-isochromene-3-carbaldehyde (Intermediate G20.1, 716 mg, 3.68 mmol) in THF (8 ml) was added followed by a degassed solution of K3PO4H2O (1,795 ml, 7.36 mmol) in water (8 ml) and the resulting mixture stirred at rt overnight. The reaction mixture was partitioned between 1M HCl (15 ml) and the same amount of AcOEt. The organic layer was anhydrified over Na2SO4, evaporated in vacuo and purified via reverse phase chromatography with a Biotage C18 SNAP 120 g column (Phase A, water 95%, ACN 5%, formic acid 0.1%); Phase B ACN 95%, water 5%, formic acid 0.1%) to give the title compound (821 mg, 94% yield).
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