Reaction SMILES: [Si:1]([O:8][C@@H:9]([CH2:28][O:29][CH3:30])[CH2:10][O:11][C:12]1[CH:13]=[CH:14][C:15]([NH:18][C:19]2[C:20](=[O:27])[N:21]([CH3:26])[N:22]=[C:23](Cl)[CH:24]=2)=[N:16][CH:17]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C([O:34][CH2:35][C:36]1[C:41](B2OC(C)(C)C(C)(C)O2)=[CH:40][CH:39]=[CH:38][C:37]=1[N:51]1[N:60]=[CH:59][C:58]2[C:53](=[C:54]([F:65])[CH:55]=[C:56]([C:61]([CH3:64])([CH3:63])[CH3:62])[CH:57]=2)[C:52]1=[O:66])(=O)C.CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.[O-]P([O-])([O-])=O.[K+].[K+].[K+].[OH-].[Na+]>C(O)CCC.C1COCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].O>[C:61]([C:56]1[CH:57]=[C:58]2[C:53](=[C:54]([F:65])[CH:55]=1)[C:52](=[O:66])[N:51]([C:37]1[CH:38]=[CH:39][CH:40]=[C:41]([C:23]3[CH:24]=[C:19]([NH:18][C:15]4[CH:14]=[CH:13][C:12]([O:11][CH2:10][C@@H:9]([O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])[CH2:28][O:29][CH3:30])=[CH:17][N:16]=4)[C:20](=[O:27])[N:21]([CH3:26])[N:22]=3)[C:36]=1[CH2:35][OH:34])[N:60]=[CH:59]2)([CH3:64])([CH3:62])[CH3:63]
Reactant: COC[C@@H](COc1ccc(Nc2cc(Cl)nn(C)c2=O)nc1)O[Si](C)(C)C(C)(C)C
Reactant: CC(=O)OCc1c(B2OC(C)(C)C(C)(C)O2)cccc1-n1ncc2cc(C(C)(C)C)cc(F)c2c1=O
Agent: [Pd]
Agent: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)C2CCCCC2)c(C(C)C)c1
Agent: O=C(/C=C/c1ccccc1)/C=C/c1ccccc1
Solvent: C1CCOC1
Solvent: O
Solvent: CCCCO
Product: COC[C@@H](COc1ccc(Nc2cc(-c3cccc(-n4ncc5cc(C(C)(C)C)cc(F)c5c4=O)c3CO)nn(C)c2=O)nc1)O[Si](C)(C)C(C)(C)C
Temperature: 110 °C
Reaction time: 20 h
Yield: 74.5 %

Procedure:
In a 50 mL test tube, (S)-4-(5-(2-(tert-butyldimethylsilyloxy)-3-methoxypropoxy)pyridin-2-ylamino)-6-chloro-2-methylpyridazin-3(2H)-one (178 mg, 391 μmol) and 2-(6-tert-butyl-8-fluoro-1-oxophthalazin-2(1H)-yl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl acetate (332 mg, 469 μmol) were combined in n-butanol (4 ml) to give a orange solution. 1 mL of water was added and the reaction mixture was purged with argon. X-PHOS (18.6 mg, 39.1 μmol) and potassium phosphate tribasic (166 mg, 782 μmol) were added. After argon was bubbled through the reaction mixture for 5 min. bis(dibenzylideneacetone)-palladium (0) (11.2 mg, 19.6 μmol) was added. The resulting suspension was heated in a oil bath at 110° C. for 1.5 hours. No (S)-4-(5-(2-(tert-butyldimethylsilyloxy)-3-methoxypropoxy)-pyridin-2-ylamino)-6-chloro-2-methylpyridazin-3(2H)-one remained by LCMS. Two main products were observed by LCMS, acetylated and deacetylated product. The reaction mixture was allowed to cool to 25° C. overnight. The reaction mixture was concentrated to small volume, poured into 75 mL H2O and extracted with EtOAc (3×75 mL). The organic layers were dried over Na2SO4 and concentrated in vacuo. The crude material was purified by flash chromatography (silica gel, 24 g, 20% to 60% EtOAc in hexanes) to afford 2 product peaks. These were combined and conc. to give 290 mg of a 1:1 mixture of acetylated and deacetylated product. This mixture was taken up in 15 mL THF and treated with 2 mL of 1N NaOH. The reaction mixture was heated to 60° C. and stirred for 20 h. Mostly complete by tlc. The reaction mixture was poured into 100 mL H2O and extracted with EtOAc (3×50 mL). The combined organic extracts were washed with brine, dried over MgSO4 and concentrated in vacuo. The crude material was purified by flash chromatography (silica gel, 40 g, 20% to 70% EtOAc in hexanes) to afford 217 mg of the desired product (75% yield). (M+H)+=745 m/e.