Reaction SMILES: Br[C:2]1[CH:14]=[CH:13][C:12]([C:15]([NH2:17])=[O:16])=[C:11]2[C:3]=1[C:4]1[CH2:5][CH2:6][CH:7]([CH2:18][OH:19])[CH2:8][C:9]=1[NH:10]2.[C:20]([C:24]1[CH:25]=[C:26]2[C:30](=[CH:31][CH:32]=1)[C:29](=[O:33])[N:28]([C:34]1[CH:39]=[CH:38][CH:37]=[C:36](B3OC(C)(C)C(C)(C)O3)[C:35]=1[CH3:49])[C:27]2=[O:50])([CH3:23])([CH3:22])[CH3:21].P([O-])([O-])([O-])=[O:52].[K+].[K+].[K+].Cl>C1(C)C=CC=CC=1.C(O)C.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>[C:20]([C:24]1[CH:32]=[CH:31][C:30]([C:29](=[O:33])[NH:28][C:34]2[CH:39]=[CH:38][CH:37]=[C:36]([C:2]3[CH:14]=[CH:13][C:12]([C:15](=[O:16])[NH2:17])=[C:11]4[C:3]=3[C:4]3[CH2:5][CH2:6][CH:7]([CH2:18][OH:19])[CH2:8][C:9]=3[NH:10]4)[C:35]=2[CH3:49])=[C:26]([CH:25]=1)[C:27]([OH:50])=[O:52])([CH3:22])([CH3:23])[CH3:21]
Reactant: O=P([O-])([O-])[O-]
Reactant: NC(=O)c1ccc(Br)c2c3c([nH]c12)CC(CO)CC3
Reactant: Cc1c(B2OC(C)(C)C(C)(C)O2)cccc1N1C(=O)c2ccc(C(C)(C)C)cc2C1=O
Agent: c1ccc([P](c2ccccc2)(c2ccccc2)[Pd]([P](c2ccccc2)(c2ccccc2)c2ccccc2)([P](c2ccccc2)(c2ccccc2)c2ccccc2)[P](c2ccccc2)(c2ccccc2)c2ccccc2)cc1
Agent: Cl
Agent: [K+]
Solvent: Cc1ccccc1
Solvent: CCO
Product: Cc1c(NC(=O)c2ccc(C(C)(C)C)cc2C(=O)O)cccc1-c1ccc(C(N)=O)c2[nH]c3c(c12)CCC(CO)C3
Temperature: 100 °C

Procedure:
A mixture of 5-bromo-2-(hydroxymethyl)-2,3,4,9-tetrahydro-1H-carbazole-8-carboxamide (Intermediate 30-3(a), 50 mg, 0.155 mmol), 5-tert-butyl-2-(2-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)isoindoline-1,3-dione (Intermediate 50-11, 97 mg, 0.232 mmol), 2 M aqueous tripotassium phosphate (0.232 mL, 0.464 mmol), and tetrakis(triphenylphosphine)palladium (8.9 mg, 7.7 μmol) in toluene (3 mL) and ethanol (1 mL) was heated at 100° C. in a sealed tube overnight. The mixture was cooled to rt, treated with 1 M hydrochloric acid, extracted with EtOAc, and the organic phase was dried and concentrated to provide 5-tert-butyl-2-(3-(8-carbamoyl-2-(hydroxymethyl)-2,3,4,9-tetrahydro-1H-carbazol-5-yl)-2-methylphenylcarbamoyl)benzoic acid (Mass spectrum m/z 554.4 (M+H)+). Without purification, this material was dissolved in acetic acid (4 mL) and heated at 100° C. for 2 h, then was concentrated. The residue was purified by column chromatography (eluting with a gradient from DCM to 90:9:1 DCM-methanol-28% aqueous ammonium hydroxide), followed by purification by preparative HPLC. The appropriate effluent fractions were made basic with NaHCO3 (aq) and extracted with DCM, dried and concentrated to provide 5-(3-(5-tert-butyl-1,3-dioxoisoindolin-2-yl)-2-methylphenyl)-2-(hydroxymethyl)-2,3,4,9-tetrahydro-1H-carbazole-8-carboxamide (Example 31-2) as a light yellow solid (18 mg, 18%). 1H NMR (400 MHz, chloroform-d) δ 10.05 (1H, s), 7.98-8.02 (1H, m), 7.86-7.91 (1H, m), 7.79-7.84 (1H, m), 7.33-7.45 (4H, m), 7.24-7.28 (2H, m), 6.89-6.94 (1H, m), 3.56-3.71 (2H, m), 2.91 (1H, dd, J=16.70, 4.83 Hz), 2.48-2.61 (1H, m), 1.99-2.10 (2H, m), 1.88-1.99 (2H, m), 1.86 (3H, s), 1.43-1.55 (2H, m), 1.41 (9H, s). Mass spectrum m/z 536.3 (M+H)+. Also obtained was (5-(3-(5-tert-butyl-1,3-dioxoisoindolin-2-yl)-2-methylphenyl)-8-carbamoyl-2,3,4,9-tetrahydro-1H-carbazol-2-yl)mEtOAc (Example 31-3) as a light yellow solid (15 mg, 14%). 1H NMR (400 MHz, chloroform-d) δ 10.05 (1H, s), 7.97-8.05 (1H, m), 7.86-7.91 (1H, m), 7.79-7.84 (1H, m), 7.33-7.41 (3H, m), 7.26-7.28 (1H, m), 4.00-4.13 (2H, m), 2.90 (2H, td, J=10.88, 5.05 Hz), 2.46-2.71 (2H, m), 2.12-2.34 (2H, m), 2.08 (4H, s), 1.87 (3H, d, J=7.03 Hz), 1.45-1.54 (1H, m), 1.41 (9H, s). Mass spectrum m/z 578.3 (M+H)+.