Br[C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([Cl:11])[CH:10]=1)[NH:7][N:6]=[C:5]2[CH2:12][CH3:13].[C:14](=O)([O-:16])[O-:15].[Na+].[Na+]>O1CCOCC1.O.CC1C(P(C2C([CH2-])=CC=CC=2)C2C(C)=CC=CC=2)=CC=CC=1.CC1C(P(C2C([CH2-])=CC=CC=2)C2C(C)=CC=CC=2)=CC=CC=1.CC(O)=O.CC(O)=O.[Pd].[Pd].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[Mo]>[Cl:11][C:9]1[CH:10]=[C:2]([C:14]([OH:16])=[O:15])[CH:3]=[C:4]2[C:8]=1[NH:7][N:6]=[C:5]2[CH2:12][CH3:13]
To a microwave tube were added 5-bromo-7-chloro-3-ethyl-1H-indazole (127.0 mg, 0.49 mmol) dissolved in dioxane (1.0 mL). The Hermann's catalyst ((trans-Bis(acetato)bis[o-(di-o-tolylphosphino)benzyl]dipalladium(II))) (23.0 mg, 0.024 mmol) and molybdenum hexacarbonyl (64.4 mg, 0.244 mmol) were added followed by a solution of sodium carbonate (156 mg, 1.47 mmol) in water (2.0 mL). Separation occurs within the vessel. The mixture was stirred for 20 seconds and then the mixture was heated to 165° C. for 15 minutes under mircrowave irradiation with the absorption setting at very high. The reaction was stopped and the vessel was vented before handling. The mixture was filtered and washed with EtOAc. The filtrate was concentrated and the residue was re-dissolved with water. The solution was then acidified to pH ˜3. The solid was collected and dried to afford 7-chloro-3-ethyl-1H-indazole-5-carboxylic acid as a solid (95.0 mg, 86.4%).
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