Reaction SMILES: C(OC([C:6]1[CH:11]=[CH:10][C:9](B(O)O)=CC=1)=O)C.NC1CC(C(N(CCC)CCC)=O)=CC2C=CC(Br)=CC=2N=1.COC(C1C=CC(B(O)O)=CC=1)=O.[C:50](=[O:53])([O-])[O-:51].[K+].[K+].[C:56]([O:60][C:61]([NH:63][C:64]1[CH2:65][C:66]([C:86](=[O:102])[N:87]([CH2:91][CH2:92][CH2:93][O:94][Si:95]([C:98]([CH3:101])([CH3:100])[CH3:99])([CH3:97])[CH3:96])[CH2:88][CH2:89][CH3:90])=[CH:67][C:68]2[CH:74]=[CH:73][C:72]([C:75]3[CH:85]=[CH:84][C:78]([C:79]([O:81][CH2:82][CH3:83])=[O:80])=[CH:77][CH:76]=3)=[CH:71][C:69]=2[N:70]=1)=[O:62])([CH3:59])([CH3:58])[CH3:57]>C(#N)C.CCOC(C)=O.ClCCl.C(O)(C(F)(F)F)=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH2:63][C:64]1[CH2:65][C:66]([C:86](=[O:102])[N:87]([CH2:91][CH2:92][CH2:93][OH:94])[CH2:88][CH2:89][CH3:90])=[CH:67][C:68]2[CH:74]=[CH:73][C:72]([C:75]3[CH:76]=[CH:77][C:78]([CH2:79][C:50]([O:51][CH2:9][CH:10]4[CH2:6][CH2:11]4)=[O:53])=[CH:84][CH:85]=3)=[CH:71][C:69]=2[N:70]=1.[C:56]([O:60][C:61]([NH:63][C:64]1[CH2:65][C:66]([C:86](=[O:102])[N:87]([CH2:91][CH2:92][CH2:93][O:94][Si:95]([C:98]([CH3:99])([CH3:101])[CH3:100])([CH3:96])[CH3:97])[CH2:88][CH2:89][CH3:90])=[CH:67][C:68]2[CH:74]=[CH:73][C:72]([C:75]3[CH:85]=[CH:84][C:78]([C:79]([O:81][CH2:82][CH3:83])=[O:80])=[CH:77][CH:76]=3)=[CH:71][C:69]=2[N:70]=1)=[O:62])([CH3:57])([CH3:58])[CH3:59]
Reactant: O=C([O-])[O-]
Reactant: CCOC(=O)c1ccc(B(O)O)cc1
Agent: c1ccc([P](c2ccccc2)(c2ccccc2)[Pd]([P](c2ccccc2)(c2ccccc2)c2ccccc2)([P](c2ccccc2)(c2ccccc2)c2ccccc2)[P](c2ccccc2)(c2ccccc2)c2ccccc2)cc1
Agent: CCCN(CCC)C(=O)C1=Cc2ccc(Br)cc2N=C(N)C1
Agent: CCCN(CCCO[Si](C)(C)C(C)(C)C)C(=O)C1=Cc2ccc(-c3ccc(C(=O)OCC)cc3)cc2N=C(NC(=O)OC(C)(C)C)C1
Solvent: O=C(O)C(F)(F)F
Solvent: CC#N
Solvent: ClCCl
Product: CCCN(CCCO)C(=O)C1=Cc2ccc(-c3ccc(CC(=O)OCC4CC4)cc3)cc2N=C(N)C1
Temperature: 100 °C
Reaction time: 1 h
Yield: 31 %

Procedure:
Cyclopropylmethyl 2-(4-((1E,4E)-2-amino-4-((3-hydroxypropyl)(propyl)carbamoyl)-3H-benzo[b]azepin-8-yl)phenyl)acetate (31%) was prepared as follows, substituting cyclopropylmethyl 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetate for 4-(ethoxycarbonyl)phenylboronic acid. Ethyl 4-((1E,4E)-2-(tert-butoxycarbonylamino)-4-((3-(tert-butyldimethylsilyloxy)propyl)(propyl)carbamoyl)-3H-benzo[b]azepin-8-yl)benzoate (44%) was prepared as follows, substituting tert-butyl (1E,4E)-8-bromo-4-((3-(tert-butyldimethylsilyloxy)propyl)(propyl)carbamoyl)-3H-benzo[b]azepin-2-ylcarbamate for 1E,4E)-2-amino-8-bromo-N,N-dipropyl-3H-benzo[b]azepine-4-carboxamide and 4-(ethoxycarbonyl)phenylboronic acid for 4-(methoxycarbonyl)phenylboronic acid. (1E,4E)-2-amino-8-bromo-N,N-dipropyl-3H-benzo[b]azepine-4-carboxamide (75.0 mgs, 0.206 mmol), 4-(methoxycarbonyl)phenylboronic acid (55.6 mgs, 0.309 mmol, tetrakis(triphenylphosphine)palladium(0) (23.8 mgs, 0.021 mmol), 2M aqueous potassium carbonate (0.309 ml, 0.618 mmol) were combined in 2 mls of acetonitrile in a microwave reaction vial. This mixture was heated in a microwave to 100° C. for 30 minutes. The mixture was then diluted with EtOAc, washed twice with brine, dried over sodium sulfate, and concentrated under reduced pressure. Preparative thin layer chromatography (2×0.5 mm plates, 7% MeOH/DCM) was then used. Ethyl 4-((1E,4E)-2-(tert-butoxycarbonylamino)-4-((3-(tert-butyldimethylsilyloxy)propyl)(propyl)carbamoyl)-3H-benzo[b]azepin-8-yl)benzoate (0.050 g, 0.075 mmol) was dissolved in 2 mls of dichloromethane and 0.5 ml of TFA. After about one hour, the mixture was concentrated under reduced pressure and the resulting residue was then re-dissolved in dichloromethane and 1 ml of concentrated ammonium hydroxide added and the mixture vigorously stirred for 15 minutes. This mixture was then diluted with water, extracted with dichloromethane (2×), extracts dried over sodium sulfate and concentrated under reduced pressure. Preparative thin layer chromatography (2×0.5 mm plates, 10% MeOH/DCM/0.5% NH4OH) was used. 1H NMR (400 MHz, CDCl3) δ 7.59-7.65 (m, 2H), 7.47-7.51 (m, 1H), 7.28-7.40 (m, 4H), 6.88 (s, 1H), 5.18 (br s, 1H), 3.92-3.99 (m, 2H), 3.58-3.72 (m, 6H), 3.43-3.53 (m, 2H), 2.83 (s, 2H), 1.79-1.88 (m, 2H), 1.65-1.77 (m, 2H), 1.08-1.20 (m, 1H), 0.90-0.98 (m, 3H), 0.53-0.60 (m, 2H), 0.24-0.31 (m, 2H); m/z (APCI-pos) M+1=490.2.