1,4-Dioxane → 6-(3-Methylpyridin-2-yl)-2-(4-(trifluoromethyl)phenyl)-1,2-dihydroindazol-3-one

HRID 270687Notes

Reaction equation

HRID 270687 reaction equation
Br[C:2]1[CH:10]=[C:9]2[C:5]([C:6](=[O:21])[N:7]([C:11]3[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=3)[NH:8]2)=[CH:4][CH:3]=1.[Li+].[Cl-].O1[CH2:29][CH2:28]OCC1>C1(P([Pd-3](Cl)(Cl)(P(C2C=CC=CC=2)C2C=CC=CC=2)[C-]2C=CC=C2)C2C=CC=CC=2)C=CC=CC=1.[CH-]1C=CC=C1.[Fe+2].[Cu]I>[CH3:4][C:5]1[C:6]([C:2]2[CH:10]=[C:9]3[C:5]([C:6](=[O:21])[N:7]([C:11]4[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=4)[NH:8]3)=[CH:4][CH:3]=2)=[N:7][CH:11]=[CH:28][CH:29]=1

Participants

6

Reactant 3

HCID 312751,4-DioxaneHCID 433294Lithium ChlorideHCID 692027741,2-Dihydro-6-bromo-2-(4-trifluoromethylphenyl)-3H-indazol-3-one

Product 1

HCID 112108736-(3-Methylpyridin-2-yl)-2-(4-(trifluoromethyl)phenyl)-1,2-dihydroindazol-3-oneYield 54%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178479788HCID 178479788, compoundCatalyst

Procedure

The product of Example 1, Step 4 (0.35 g, 1 mmol)), bis(diphenylphosphino) ferrocenyl palladium(II) dichloride 0) (40 mg), CuI (19 mg, 0.1 mmol), LiCl (126 mg, 3 mmol), 3-methyl-2-(tri-nbutylstannyl)pyridine (530 mg, 1.4 mmol) and dioxane (4 mL) were heated at 150° C. for 15 min under microwave irradiation. The resulting mixture was purified by column chromatography (silica; EtAc:hexane 1:2->EtAc) to give 0.2 g (54%) of the title compound as a colourless solid. 1H NMR (360 MHz, DMSO): 2.5 (3H, s), 7.30-7.40 (2H, m), 7.50 (1H, m), 7.78 (1H, d, J 7.7 Hz), 7.85 (1H, d, J 8.0 Hz), 7.90 (2H, d, J 8.5 Hz), 8.19 (2H, d, J 8.5 Hz), 8.53 (1H, d, J 4.6 Hz), 10.8 (1H, s).

Workup

  1. customThe resulting mixture was purified by column chromatography (silica; EtAc:hexane 1:2->EtAc)

Sources & evidence

ORD record
ord-8d63a6f28074476e9bb2f5a93886d699
Source dataset
uspto-grants-2008_11
Patent number
US07449585B2

Reaction notes

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