Reaction SMILES: C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=C(S([O-])(=O)=O)C=2OC)CCCCC1.[Na+].C([O-])([O-])=O.[Cs+].[Cs+].B([C:44]1[CH:45]=[C:46]([CH:50]=[CH:51][CH:52]=1)[C:47]([OH:49])=[O:48])(O)O.Br[C:54]1[N:59]=[C:58]2[C:60]([C:70]([NH:72][CH3:73])=[O:71])=[C:61]([C:63]3[CH:68]=[CH:67][C:66]([F:69])=[CH:65][CH:64]=3)[O:62][C:57]2=[CH:56][CH:55]=1>CN(C=O)C.O>[F:69][C:66]1[CH:65]=[CH:64][C:63]([C:61]2[O:62][C:57]3[C:58](=[N:59][C:54]([C:44]4[CH:45]=[C:46]([CH:50]=[CH:51][CH:52]=4)[C:47]([OH:49])=[O:48])=[CH:55][CH:56]=3)[C:60]=2[C:70](=[O:71])[NH:72][CH3:73])=[CH:68][CH:67]=1
Reactant: O=C(O)c1cccc(B(O)O)c1
Reactant: CNC(=O)c1c(-c2ccc(F)cc2)oc2ccc(Br)nc12
Agent: COc1ccc(S(=O)(=O)[O-])c(OC)c1-c1ccccc1P(C1CCCCC1)C1CCCCC1
Agent: O=C([O-])[O-]
Agent: [Cs+]
Solvent: O
Solvent: CN(C)C=O
Product: CNC(=O)c1c(-c2ccc(F)cc2)oc2ccc(-c3cccc(C(=O)O)c3)nc12
Temperature: 60 °C
Reaction time: 1 h

Procedure:
Sodium 2′-(dicyclohexylphosphino)-2,6-dimethoxybiphenyl-3-sulfonate (8.8 mg, 0.017 mmol), PdOAc2 (1.9 mg, 8.6 μmol), Cs2CO3 (84 mg, 0.26 mmol), 3-boronobenzoic acid (21 mg, 0.13 mmol) was added to a stirring solution of 5-bromo-2-(4-fluorophenyl)-N-methylfuro[3,2-b]pyridine-3-carboxamide (30 mg, 0.086 mmol) in DMF (1.6 mL) and Water (160 μL). It was degassed and heated to 60° C. and allowed to stir for 1 hour. The mixture was diluted with ethyl acetate and washed with 1M HCl, and sat NaCl. The organic phase was dried over Na2SO4, filtered and concentrated to give 3-(2-(4-fluorophenyl)-3-(methylcarbamoyl)furo[3,2-b]pyridin-5-yl)benzoic acid. The residue was diluted with DMF (1.6 mL) and treated with HATU (49 mg, 0.13, mmol), 1-(pyridin-2-yl)cyclopropanamine dihydrochloride (27 mg, 0.13 mmol), followed by DIEA (75 μL, 0.43 mmol) at room temperature. The reaction was allowed to stir for 1 hr. The mixture was diluted with EtOAc and washed with 1M NaOH, and sat NaCl. The organic phase was dried over Na2SO4, filtered and concentrated and was purified by preparative reverse phase HPLC on a C18 column using a suitably buffered H2O/CH3CN gradient, and concentrated to give the expected product 2-(4-fluorophenyl)-N-methyl-5-(3-(1-(pyridin-2-yl)cyclopropylcarbamoyl)phenyl)furo[3,2-b]pyridine-3-carboxamide (12 mg, 0.023 mmol, 27% yield) consistent by LCMS and NMR. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.44 (1H, s), 9.09-9.18 (1H, m), 8.73 (1H, s), 8.46 (1H, d), 8.39 (1H, d), 8.27-8.35 (3H, m), 8.19 (1H, d, J=8.78 Hz), 8.01 (1H, d), 7.65-7.74 (2H, m), 7.39-7.46 (3H, m), 7.13-7.20 (1H, m), 2.98 (3H, d, J=4.77 Hz). LC-MS retention time: 1.50 min; m/z (MH+): 507. LC data was recorded on a Shimadzu LC-10AS liquid chromatograph equipped with a Waters Xterra MS 7u C18 3.0×50 mm column using a SPD-10AV UV-Vis detector at a detector wave length of 220 nM. The elution conditions employed a flow rate of 5 ml/min, a gradient of 100% solvent A/0% solvent B to 0% solvent A/100% solvent B, a gradient time of 3 min, a hold time of 1 min, and an analysis time of 4 mM where solvent A was 5% acetonitrile/95% H2O/10 mM ammonium acetate and solvent B was 5% H2O/95% acetonitrile/10 mM ammonium acetate. MS data was determined using a Micromass Platform for LC in electrospray mode. Additional HPLC method: Solvent A=5% MeOH/95% H2O/10 mM ammonium bicarbonate, Solvent B=95% MeOH/5% H2O/10 mM ammonium bicarbonate, Start % B=10, Final % B=100, Gradient time=15 min, Stop time=18 min, Flow Rate=1 ml/min. Column: Phenomenex Gemini C1 C-18, 4.6×150 mm, 3 mm, Rt=25.18 min, purity=99%; Column: Waters) (bridge Phenyl column 4.6×150 mm, 3.5 mm, Rt=25.85 mM, purity=99%.