Potassium Fluoride → 3-(3-Nitro-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-4-yl)-3'-(trifluoromethyl)biphenyl-4-ol

HRID 1619688Notes

Reaction equation

I[C:2]1[CH:3]=[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:10]=2)[CH:5]=[CH:6][C:7]=1[OH:8].[N+:19]([C:22]1[C:26](B2OC(C)(C)C(C)(C)O2)=[CH:25][N:24]([CH:36]2[CH2:41][CH2:40][CH2:39][CH2:38][O:37]2)[N:23]=1)([O-:21])=[O:20].[F-].[K+]>O1CCCC1.C(P([Pd-2]P(C(C)(C)C)(C(C)(C)C)C(C)(C)C)(C(C)(C)C)C(C)(C)C)(C)(C)C>[N+:19]([C:22]1[C:26]([C:2]2[CH:3]=[C:4]([C:9]3[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:10]=3)[CH:5]=[CH:6][C:7]=2[OH:8])=[CH:25][N:24]([CH:36]2[CH2:41][CH2:40][CH2:39][CH2:38][O:37]2)[N:23]=1)([O-:21])=[O:20]

Participants

Conditions

Temperature: 65 °C

Procedure

A mixture of 3-iodo-3′-(trifluoromethyl)biphenyl-4-ol (Preparation 2, 0.5 g, 1.3 mmol), 3-nitro-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (0.42 g, 1.3 mmol), potassium fluoride (0.39 g, 0.65 mmol) in tetrahydrofuran (10 mL) was degassed. Bis-(tri-t-Butylphosphino)palladium (0) (35 mg, 0.068 mmol) was added and the reaction heated at 65° C. for 4 hours. After cooling the solvent was removed in vacuo and the residue was purified by silica gel chromatography (ethyl acetate:heptane 1:10) to provide the title compound (0.34 g, 61%) as a colourless oil.

Workup

customwas degassed
temperatureAfter cooling the solvent
customwas removed in vacuo
customthe residue was purified by silica gel chromatography (ethyl acetate:heptane 1:10)

Sources & evidence

ORD record: ord-6f17e4e55a9f49f48a1312b7f88184ed
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08772293B2

Reaction notes

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