Reaction SMILES: [NH2:1][C:2]1[CH:14]=[C:13]2[C:5]([C:6]3[CH:7]=[C:8](Br)[CH:9]=[C:10]([C:15]([NH2:17])=[O:16])[C:11]=3[NH:12]2)=[CH:4][CH:3]=1.[Cl:19][C:20]1[CH:21]=[C:22](B(O)O)[CH:23]=[CH:24][C:25]=1[OH:26].C([O-])([O-])=O.[Na+].[Na+]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(Cl)Cl.ClC1C=C(B(O)O)C=CC=1O.COCCOC>[NH2:1][C:2]1[CH:14]=[C:13]2[C:5]([C:6]3[CH:7]=[C:8]([C:22]4[CH:23]=[CH:24][C:25]([OH:26])=[C:20]([Cl:19])[CH:21]=4)[CH:9]=[C:10]([C:15]([NH2:17])=[O:16])[C:11]=3[NH:12]2)=[CH:4][CH:3]=1
Reactant: NC(=O)c1cc(Br)cc2c1[nH]c1cc(N)ccc12
Reactant: OB(O)c1ccc(O)c(Cl)c1
Agent: Cl[Pd]Cl
Agent: [Fe+2]
Agent: O=C([O-])[O-]
Solvent: COCCOC
Solvent: ClCCl
Product: NC(=O)c1cc(-c2ccc(O)c(Cl)c2)cc2c1[nH]c1cc(N)ccc12
Temperature: 85 °C
Reaction time: 0.33 h
Yield: 105.4 %

Procedure:
A 250 ml pressure flask was loaded with 7-amino-3-bromo-9H-carbazole-1-carboxamide (2.02 g, 5.31 mmol, Example 480B), 3-chloro-4-hydroxyphenylboronic acid (1.00 g, 5.80 mmol), PdCl2(dppf)-CH2Cl2 adduct (0.167 g, 0.204 mmol), Na2CO3 (2M) (8 mL, 16.00 mmol) and DME (80 mL). The flask was flushed with N2 and heated at 85° C. in an oil bath for 3 hours. LCMS after 2 h 20 min showed ˜⅔ conversion. The temperature was increased to 100° C. and heating continued for 1 hour. LCMS showed small amount of remaining starting material. 3-Chloro-4-hydroxyphenylboronic acid (80 mg, 0.46 mmol) and PdCl2(dppf)-CH2Cl2 adduct (0.050 g, 0.061 mmol) were added, the flask flushed with nitrogen again and heated to 100° C. for an additional 1 hour. The reaction mixture was partitioned between a saturated aqueous solution of NaCl and a 1:1 mixture of acetone and ethyl acetate. The aqueous layer was extracted once more with EtOAc+Acetone 1+1, the organic layer washed with brine, dried over MgSO4, filtered and concentrated to dryness. A brown precipitate formed in the aqueous layer and between the layers during the extraction. It was collected by filtration through a pad of CELITE®. The CELITE® was washed with water, dried and the filter cake then washed with acetone. LCMS analysis of this showed a small amount of product in acetone solution. This material was combined with the extracted product. The collected MgSO4 (from drying the organic layer) also had a brown precipitate mixed into it. This filter cake was washed with acetone. LCMS shows small amount of product in acetone solution. This solution was combine with main product fraction. Purification by flash column chromatography (gradient from 100% DCM to 25% DCM+75% acetone, then from (25% DCM+75% acetone) to (20% DCM+60% Acetone+20% MeOH). Product streaked badly, eluted from end of first gradient until end of second gradient. Product containing fractions were combined and evaporated to dryness to give 1.968 g 7-amino-3-(3-chloro-4-hydroxyphenyl)-9H-carbazole-1-carboxamide. HPLC retention time 6.17 min. (Sunfire C18 3.5 μm, 3.0×150 mm column, 15 min gradient, 10-100% B, 0.5 mL/min. Solvent A: 5% CH3CN—95% H2O—0.1% TFA; Solvent B: 95% CH3CN—5% H2O—0.1% TFA). HPLC purity ˜55%. MS (ESI) m/e+=352/354 (isotope pattern consistent with 1 Cl) consistent with [M+H]+. The material was used without further purification.