Reaction SMILES: Cl[C:2]1[CH:25]=[CH:24][C:5]2[C:6]3[C:10]([CH3:11])=[N:9][O:8][C:7]=3[C:12]3([N:15]=[C:16]([C:17]4[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=4)[C:4]=2[CH:3]=1)[CH2:14][CH2:13]3.F[B-](F)(F)F.C([PH+](C(C)(C)C)C(C)(C)C)(C)(C)C.P([O-])([O-])([O-])=O.[K+].[K+].[K+].CC1(C)C(C)(C)OB([C:60]2[CH:61]=[CH:62][C:63]([NH2:66])=[N:64][CH:65]=2)O1>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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[F:23][C:20]1[CH:19]=[CH:18][C:17]([C:16]2[C:4]3[CH:3]=[C:2]([C:60]4[CH:61]=[CH:62][C:63]([NH2:66])=[N:64][CH:65]=4)[CH:25]=[CH:24][C:5]=3[C:6]3[C:10]([CH3:11])=[N:9][O:8][C:7]=3[C:12]3([CH2:13][CH2:14]3)[N:15]=2)=[CH:22][CH:21]=1
Reactant: Cc1noc2c1-c1ccc(Cl)cc1C(c1ccc(F)cc1)=NC21CC1
Reactant: CC1(C)OB(c2ccc(N)nc2)OC1(C)C
Agent: [Pd]
Agent: CC(C)(C)[PH+](C(C)(C)C)C(C)(C)C
Agent: F[B-](F)(F)F
Product: Cc1noc2c1-c1ccc(-c3ccc(N)nc3)cc1C(c1ccc(F)cc1)=NC21CC1
Temperature: 100 °C
Reaction time: 3 h

Procedure:
To a 25 mL round bottom flask containing 8-chloro-6-(4-fluorophenyl)-1-methylspiro[benzo[e]isoxazolo[5,4-c]azepine-4,1′-cyclopropane] (57 mg, 0.162 mmol) was added Pd2(dba)3 (9.1 mg, 9.94 μmol), tri-tert-butylphosphonium tetrafluoroborate (6.5 mg, 0.022 mmol), potassium phosphate (77 mg, 0.363 mmol), and 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine (56 mg, 0.254 mmol). The flask was evacuated and purged with N2 (g) (3×), followed by addition of 1,4-dioxane (1 mL) and water (0.05 mL). The flask was evacuated and purged with N2 (g) (3×) and the reaction mixture was heated to 100° C. After 3 h, ˜50% conversion of starting material was observed by LC-MS analysis. The reaction mixture was cooled to room temperature and additional Pd2(dba)3 (9.1 mg, 9.94 μmol), tri-tert-butylphosphonium tetrafluoroborate (6.5 mg, 0.022 mmol), potassium phosphate (77 mg, 0.363 mmol), and 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine (56 mg, 0.254 mmol) were introduced. The mixture was subsequently heated again for an additional 24 h. LC-MS analysis after 24 h, indicated ˜80% conversion to desired product. The reaction mixture was cooled and filtered over a pad of Celite. The filter cake was washed with EtOAc (3×) and the filtrate was concentrated to give a dark brown oil. The oil was purified on Biotage system (25% EtOAc:75% Hexanes to 70% EtOAc:30% Hexanes, then isocratic 70% EtOAc:30% Hexanes). The product was concentrated to give gummy yellow solid that was contaminated with 2-amino-pyridine. The solid was triturated with IPA (1 mL) and Et2O (1 mL) and filtered. The solids were washed with ether (1 mL) and filtered. The amino pyridine (yellow color) was cleanly removed in the rinses and the product 5-(6-(4-fluorophenyl)-1-methylspiro[benzo[e]isoxazolo[5,4-c]azepine-4,1′-cyclopropane]-8-yl)pyridin-2-amine (0.032 g, 0.078 mmol, 48.3% yield) was isolated as white-solids. LC/MS m/z 411 [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ 8.16 (d, J=2.49 Hz, 1H), 7.86 (dd, J=1.97, 8.21 Hz, 1H), 7.79 (s, 1H), 7.59 (dd, J=2.60, 8.62 Hz, 1H), 7.49-7.42 (m, 2H), 7.37 (d, J=1.87 Hz, 1H), 7.24-7.15 (m, 2H), 6.49 (dd, J=0.62, 8.72 Hz, 1H), 6.14 (s, 2H), 2.54 (s, 3H), 1.28 (d, J=6.02 Hz, 4H).