Potassium Carbonate → HCID 25070234, compound

HRID 883275Notes

Reaction equation

HRID 883275 reaction equation
FC(F)(F)S(O[C:7]1[C:16]2[CH2:15][CH2:14][C@H:13]([N:17]([CH:19]([CH3:21])[CH3:20])[CH3:18])[CH2:12][C:11]=2[CH:10]=[CH:9][CH:8]=1)(=O)=O.[CH3:24][N:25]1[C:29]([CH3:30])=[C:28](B2OC(C)(C)C(C)(C)O2)[C:27]([CH3:40])=[N:26]1.C([O-])([O-])=O.[K+].[K+]>COCCOC.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH:19]([N:17]([CH3:18])[C@H:13]1[CH2:14][CH2:15][C:16]2[C:11](=[CH:10][CH:9]=[CH:8][C:7]=2[C:28]2[C:27]([CH3:40])=[N:26][N:25]([CH3:24])[C:29]=2[CH3:30])[CH2:12]1)([CH3:21])[CH3:20]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 27953111,3,5-Trimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 87509343HCID 87509343, compound

Product 1

HCID 25070234HCID 25070234, compoundYield 56%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

(S)-6-(Isopropyl(methyl)amino)-5,6,7,8-tetrahydronaphthalen-1-yl trifluoromethanesulfonate (184 mg, 0.524 mmol), 1,3,5-trimethyl-1H-pyrazole-4-boronic acid pinacol ester (142 mg, 0.602 mmol) and Pd(PPh3)4 (60 g, 0.0524 mmol) were added to a solution of K2CO3 (145 mg, 1.047 mmol) in a mixture of 1,2-dimethoxyethane (7 mL) and H2O (1 mL). The reaction mixture was purged with Ar (g) for 10 min, and warmed up to reflux. The reaction was completed in 4 h. It was allowed to reach room temperature, diluted with CH2Cl2 (20 mL) and acidified with HCl aqueous solution (10%, 30 mL). The organic layer was discarded, and the aqueous layer was taken to pH=9-10 with NaOH aqueous solution (10%). It was extracted with CH2Cl2 (3×20 mL), and the organic layer was dried over anhydrous Na2SO4, filtered and concentrated. The obtained crude was purified by flash chromatography on silica gel (5% Et3N/AcOEt), to afford 91 mg of the desired product (yellow oil, 56% yield).

Workup

  1. customThe reaction mixture was purged with Ar (g) for 10 min
  2. temperaturewarmed up
  3. temperatureto reflux
  4. customto reach room temperature
  5. additiondiluted with CH2Cl2 (20 mL)
  6. extractionIt was extracted with CH2Cl2 (3×20 mL)
  7. dry with materialthe organic layer was dried over anhydrous Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe obtained crude
  11. customwas purified by flash chromatography on silica gel (5% Et3N/AcOEt)

Sources & evidence

ORD record
ord-bf3ac58df01c486e8e4090525baa993d
Source dataset
uspto-grants-2012_08
Patent number
US08236845B2

Reaction notes

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