Reaction SMILES: [CH2:1]([O:3][C:4]([C:6]1[CH:11]=[CH:10][C:9](B(O)O)=[CH:8][CH:7]=1)=[O:5])C.NC1CC(C(N(CCC)CCC)=O)=CC2C=CC(Br)=CC=2N=1.COC(C1C=CC(B(O)O)=CC=1)=O.C(=O)([O-])[O-].[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]([N:87]([CH2:91][CH2:92][CH2:93][OH:94])[CH2:88][CH2:89][CH3:90])=[O:102])=[CH:67][C:68]2[CH:74]=[CH:73][C:72]([C:10]3[CH:11]=[C:6]4[C:7](=[CH:8][CH:9]=3)[CH2:1][O:3][C:4]4=[O:5])=[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: 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: CCOC(C)=O
Solvent: O=C(O)C(F)(F)F
Solvent: ClCCl
Product: CCCN(CCCO)C(=O)C1=Cc2ccc(-c3ccc4c(c3)C(=O)OC4)cc2N=C(N)C1
Temperature: 100 °C
Reaction time: 1 h
Yield: 36 %

Procedure:
(1E,4E)-2-Amino-N-(3-hydroxypropyl)-8-(3-oxo-1,3-dihydroisobenzofuran-5-yl)-N-propyl-3H-benzo[b]azepine-4-carboxamide (36%) was prepared as follows, substituting 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isobenzofuran-1(3H)-one 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, DMSO-d6) δ 8.08-8.13 (m, 1H), 8.03-8.06 (m, 1H), 7.74-7.78 (m, 1H), 7.41-7.45 (m, 1H), 7.32-7.36 (m, 2H), 6.91 (br s, 2H), 6.80 (s, 1H), 5.47 (s, 2H), 4.45-4.50 (m, 1H), 53.37-3.48 (m, 2H), 3.28-3.37 (m, 4H, obscured by water peak), 2.75 (s, 2H), 1.66-1.77 (m, 2H), 1.51-1.62 (m, 2H), 0.72-0.91 (m, 3H); m/z (APCI-pos) M+1=434.2.