Sodium Carbonate → 1,2-Dihydro-2-(4-trifluoromethylphenyl)-6-(3-trifluoromethyl-2-pyridinyl)-1-(2-(trimethylsilyl)ethoxymethyl)-3H-indazol-3-one

HRID 270685Notes

Reaction equation

Br[C:2]1[CH:10]=[C:9]2[C:5]([C:6](=[O:29])[N:7]([C:19]3[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][CH:20]=3)[N:8]2[CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])=[CH:4][CH:3]=1.B1(B2OC(C)(C)C(C)(C)O2)OC(C)(C)C(C)(C)O1.CC([O-])=O.[K+].Cl[C:54]1[C:59]([C:60]([F:63])([F:62])[F:61])=[CH:58][CH:57]=[CH:56][N:55]=1.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.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]>[F:28][C:25]([F:27])([F:26])[C:22]1[CH:23]=[CH:24][C:19]([N:7]2[C:6](=[O:29])[C:5]3[C:9](=[CH:10][C:2]([C:54]4[C:59]([C:60]([F:63])([F:62])[F:61])=[CH:58][CH:57]=[CH:56][N:55]=4)=[CH:3][CH:4]=3)[N:8]2[CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:17])([CH3:16])[CH3:18])=[CH:20][CH:21]=1

Participants

Conditions

Temperature: 100 °C

Procedure

The product of Step 5 (1.3 g, 2.6 mmol), was dissolved in dioxane (10 mL) and flushed with N2. Bis(pinacolato)diboron (680 mg, 2.6 mmol), bis(diphenylphosphino)ferrocenyl palladium(II) dichloride (60 mg) and KOAc (380 mg, 3.9 mmol) were added. The mixture was stirred at 100° C. overnight. 2-Chloro-3-trifluoromethylpyridine (470 mg, 2.6 mmol), bis(diphenylphosphino)ferrocenyl palladium(II) dichloride (20 mg) and saturated Na2CO3 solution (1 mL) were added, and the mixture heated at reflux for a further 18 h. Purification by column chromatography gave 0.2 g of product as an oil.

Workup

customflushed with N2
temperaturethe mixture heated
temperatureat reflux for a further 18 h
customPurification by column chromatography

Sources & evidence

ORD record: ord-966c5ef759ed41eaadad4c4e9772a7c0
Source dataset: uspto-grants-2008_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07449585B2

Reaction notes

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