Potassium Carbonate → HCID 90460873, compound

HRID 1846249Notes

Reaction equation

HRID 1846249 reaction equation
I[C:2]1[N:6]([CH:7]2[CH2:12][CH2:11][CH2:10][CH2:9][O:8]2)[N:5]=[C:4]([CH3:13])[C:3]=1[C:14]([O:16][CH2:17][CH3:18])=[O:15].[CH3:19][O:20][CH2:21][CH2:22][O:23][C:24]1[CH:25]=[C:26](B2OC(C)(C)C(C)(C)O2)[CH:27]=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:29]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.O.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]>[CH3:19][O:20][CH2:21][CH2:22][O:23][C:24]1[CH:25]=[C:26]([C:2]2[N:6]([CH:7]3[CH2:12][CH2:11][CH2:10][CH2:9][O:8]3)[N:5]=[C:4]([CH3:13])[C:3]=2[C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:27]=[C:28]([C:30]([F:31])([F:32])[F:33])[CH:29]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 90456201HCID 90456201, compoundHCID 90461215HCID 90461215, compound

Product 1

HCID 90460873HCID 90460873, compoundYield 74.2%

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of (R/S) ethyl 5-iodo-3-methyl-1-(oxan-2-yl)-1H-pyrazole-4-carboxylate (440 mg, 1.21 mmol, 1.00 equiv), 2-[3-(2-methoxyethoxy)-5-(trifluoromethyl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (500 mg, 1.44 mmol, 0.97 equiv), Pd(dppf)Cl2 (132 mg, 0.18 mmol, 0.12 equiv) and potassium carbonate (497 mg, 3.60 mmol, 2.40 equiv) in 1,4-dioxane (50 mL) and water (5 mL) was stirred under nitrogen at 100° C. for 3 h. The resulting mixture was cooled to room temperature then diluted with water (30 mL). The resulting solution was extracted with 3×30 mL of ethyl acetate. The combined organic layers were washed with 3×100 mL of brine, dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was purified on a silica gel column eluted with 0-20% of ethyl acetate in petroleum ether to give 410 mg (74%) of (R/S) ethyl 5-(3-(2-methoxyethoxy)-5-(trifluoromethyl)phenyl)-3-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazole-4-carboxylate as a yellow oil. LCMS (method D, ESI): RT=1.70 min, m/z=457.0 [M+H]+.

Workup

  1. temperatureThe resulting mixture was cooled to room temperature
  2. extractionThe resulting solution was extracted with 3×30 mL of ethyl acetate
  3. washThe combined organic layers were washed with 3×100 mL of brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under vacuum
  6. customThe residue was purified on a silica gel column
  7. washeluted with 0-20% of ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-0b48869df2004233a215594283f22c35
Source dataset
uspto-grants-2015_02
Patent number
US08952026B2

Reaction notes

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