Reaction SMILES: [F:1][C:2]1[C:7]2[C:8]([C:18](=[O:21])[NH:19][CH3:20])=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=3)[O:10][C:6]=2[CH:5]=[CH:4][C:3]=1[C:22]1[C:23]([CH3:33])=[CH:24][C:25]([O:31][CH3:32])=[C:26]([CH:30]=1)[C:27]([OH:29])=O.C(N(C(C)C)C(C)C)C.[NH:43]1[C:51]2[CH:50]=[CH:49][N:48]=[CH:47][C:46]=2[N:45]=[C:44]1[C:52]1([NH2:55])[CH2:54][CH2:53]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.C(#N)C>[NH:43]1[C:51]2[CH:50]=[CH:49][N:48]=[CH:47][C:46]=2[N:45]=[C:44]1[C:52]1([NH:55][C:27]([C:26]2[C:25]([O:31][CH3:32])=[CH:24][C:23]([CH3:33])=[C:22]([C:3]3[CH:4]=[CH:5][C:6]4[O:10][C:9]([C:11]5[CH:12]=[CH:13][C:14]([F:17])=[CH:15][CH:16]=5)=[C:8]([C:18]([NH:19][CH3:20])=[O:21])[C:7]=4[C:2]=3[F:1])[CH:30]=2)=[O:29])[CH2:53][CH2:54]1
Reactant: CNC(=O)c1c(-c2ccc(F)cc2)oc2ccc(-c3cc(C(=O)O)c(OC)cc3C)c(F)c12
Reactant: NC1(c2nc3cnccc3[nH]2)CC1
Agent: CN(C)C(On1nnc2cccnc21)=[N+](C)C
Agent: F[P-](F)(F)(F)(F)F
Solvent: CC#N
Solvent: CCN(C(C)C)C(C)C
Solvent: CN(C)C=O
Product: CNC(=O)c1c(-c2ccc(F)cc2)oc2ccc(-c3cc(C(=O)NC4(c5nc6cnccc6[nH]5)CC4)c(OC)cc3C)c(F)c12
Temperature: 25 °C
Reaction time: 8 h
Yield: 49.4 %

Procedure:
To a screw cap vial was added 5-(4-fluoro-2-(4-fluorophenyl)-3-(methylcarbamoyl)benzofuran-5-yl) 2-methoxy-4-methylbenzoic acid (45.1 mg, 0.1 mmol) in DMF (1.8 mL) along with N-ethyl-N-isopropylpropan-2-amine (0.087 mL, 0.500 mmol), 1-(1H-imidazo[4,5-c]pyridin-2-yl)cyclopropanamine (26.1 mg, 0.150 mmol) and finally 2-(3H-[1,2,3]triazolo[4,5-b]pyridin-3-yl)-1,1,3,3-tetramethylisouronium hexafluorophosphate(V) (114 mg, 0.300 mmol). The vial was capped and shaken overnight at room temperature. The crude reaction mixture was further diluted with 2 mL of acetonitrile and purified using a Shimadzu preparative HPLC employing acetonitrile/water/trifluoroacetic acid where solvent A was 10% acetonitrile/90% water/0.1% trifluoroacetic acid and solvent B was 10% water/90% acetonitrile/0.1% trifluoroacetic acid with a Phenomenex-Luna 10 μm C18 30×100 mm column at a gradient of 30-100% B and a flow rate of 30 mL/min. over 10 minutes with a 15 minute hold. The desired material was free based (DCM/bicarb), dried over magnesium sulfate, decanted, and evaporated to dryness to give 30 mgs (48% yield) of 5-(5-(1-(1H-imidazo[4,5-c]pyridin-2-yl)cyclopropylcarbamoyl)-4-methoxy-2-methylphenyl)-4-fluoro-2-(4-fluorophenyl)-N-methylbenzofuran-3-carboxamide as a yellow solid. 1H NMR (500 MHz, CD3OD) δ ppm 1.49-1.59 (m, 2 H), 1.76-1.85 (m, 2 H), 2.25 (br. s., 3 H), 2.90 (s, 3 H), 3.99-4.06 (m, 3 H), 7.13 (s, 1 H), 7.16-7.28 (m, 3 H), 7.38-7.52 (m, 2 H), 7.81-7.92 (m, 3 H), 8.20 (d, J=5.80 Hz, 1H), 8.69 (s, 1 H). LCMS rt=2.325 min., m/z 608.3 (M+H). HPLC rt=6.626 min. (Sunfire C18), 96.5% purity and 10.973 min. (Gemini C18), 99.5% purity. The LC/MS data was obtained on a Shimadzu analytical LC/Micromass Platform LC (ESI+) at 220 nm using the following set of conditions: Phenomenex Luna 3 μm C18, 2×50 mm column, with a gradient of 0-100% B (B=90% HPLC grade acetonitrile/0.1% trifluoroacetic acid/10% HPLC grade water), (A=90% HPLC grade water/0.1% trifluoroacetic acid/10% HPLC grade acetonitrile), in 4 minutes with a 1 minute hold at a rate of 0.8 mL/minute. HPLC purity was determined using a Shimadzu analytical LC at 254 nm and 256 nm with a Waters Sunfire C18 3.5 μm 4.6×150 mm column employing water/acetonitrile/0.1% trifluoroacetic acid with a gradient of 10-100% B (B=95% HPLC grade acetonitrile/0.1% trifluoroacetic acid/5% HPLC grade water), (A=95% HPLC grade water/0.1% trifluoroacetic acid/5% HPLC grade acetonitrile), in 10 minutes with a 10 minute hold at a rate of 1 mL/minute. The HPLC purity was then confirmed with an orthogonal solvent system and column using a Shimadzu analytical LC with a Phenomenex Gemini C18 3.0 μm 4.6×150 mm column employing water/methanol/10 mM ammonium bicarbonate with a gradient of 10-100% B (B=95% HPLC grade methanol/10 mM ammonium bicarbonate/5% HPLC grade water), (A=95% HPLC grade water/10 mM ammonium bicarbonate/5% HPLC grade methanol), in 10 minutes with a 10 minute hold at a rate of 1 mL/minute.