Reaction SMILES: CC(N=NC(C#N)(C)C)([C:4]#[N:5])C.C1C(=O)N(Br)C(=O)C1.[F:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]2[O:54][C:31]3=[N:32][CH:33]=[C:34]([C:36]4[CH:37]=[C:38]([CH:51]=[CH:52][CH:53]=4)[C:39]([NH:41][C:42]4([C:45]5[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=5)[CH2:44][CH2:43]4)=[O:40])[CH:35]=[C:30]3[C:29]=2[CH:55]=[O:56])=[CH:24][CH:23]=1.CN>C(Cl)(Cl)(Cl)Cl>[F:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]2[O:54][C:31]3=[N:32][CH:33]=[C:34]([C:36]4[CH:53]=[CH:52][CH:51]=[C:38]([C:39](=[O:40])[NH:41][C:42]5([C:45]6[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=6)[CH2:43][CH2:44]5)[CH:37]=4)[CH:35]=[C:30]3[C:29]=2[C:55]([NH:5][CH3:4])=[O:56])=[CH:24][CH:23]=1
Reactant: O=Cc1c(-c2ccc(F)cc2)oc2ncc(-c3cccc(C(=O)NC4(c5ccccc5)CC4)c3)cc12
Reactant: CC(C)(C#N)N=NC(C)(C)C#N
Agent: CN
Agent: O=C1CCC(=O)N1Br
Solvent: ClC(Cl)(Cl)Cl
Product: CNC(=O)c1c(-c2ccc(F)cc2)oc2ncc(-c3cccc(C(=O)NC4(c5ccccc5)CC4)c3)cc12
Reaction time: 0.5 h
Yield: 36 %

Procedure:
AIBN (3.6 mg, 0.022 mmol) and NBS (17 mg, 0.095 mmol) was added to a stirring solution of 3-(2-(4-fluorophenyl)-3-formylfuro[2,3-b]pyridin-5-yl)-N-(1-phenylcyclopropyl)benzamide (35 mg, 0.073 mmol) in CCl4 (10 mL) at 95° C. It was allowed to stir for 30 min. The reaction was removed from the heat and allowed to stir for 2 min and treated with methanamine (0.184 mL, 0.367 mmol, 2M in THF). The reaction was allowed to stir for 1 hour and concentrated. The residue was diluted with EtOAc and washed with 10% sodium bisulfate, and sat NaCl. The organic phase was dried over Na2SO4, filtered and concentrated and was purified on silica gel (Biotage, EtOAc/hexanes gradient, fraction collection at λ=254 nm) to give to give the expected product 2-(4-fluorophenyl)-N-methyl-5-(3-(1-phenylcyclopropylcarbamoyl)phenyl)furo[2,3-b]pyridine-3-carboxamide (4 mg, 7.91 μmol, 11% yield) consistent by LCMS and NMR. 1H NMR (500 MHz, DMSO-d6) δ ppm 9.36 (1H, s), 8.77 (1H, d, J=2.14 Hz), 8.54-8.62 (1H, m), 8.41 (1H, d, J=2.14 Hz), 8.31 (1H, s), 8.04-8.09 (2H, m), 7.99 (1H, d), 7.95 (1H, d, J=7.63 Hz), 7.64 (1H, t, J=7.63 Hz), 7.43 (2H, t, J=8.85 Hz), 7.26-7.31 (2H, m), 7.21-7.26 (2H, m), 7.16 (1H, t), 2.87 (3H, d, J=4.88 Hz), 1.31 (4H, d, J=7.93 Hz). LC-MS retention time: 1.98 min; m/z (MH+): 506. LC data was recorded on a Shimadzu LC-10AS liquid chromatograph equipped with a Waters SunFire 5 u C18 4.6×50 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 min where solvent A was 10% acetonitrile/90% H2O/0.1% trifluoroacetic acid and solvent B was 10% H2O/90% acetonitrile/0.1% trifluoroacetic acid. 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=14.12 min, purity=95%; Column: Waters Xbridge Phenyl column 4.6×150 mm, 3.5 mm, Rt=14.45 min, purity=96%.