Potassium Carbonate → HCID 118431798, compound

HRID 2207989Notes

Reaction equation

HRID 2207989 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:8]2[N:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[Cl:19])[N:11]=[C:10]([C:20]([F:26])([F:25])[C:21]([F:24])([F:23])[F:22])[CH2:9]2)[CH:5]=[CH:6][CH:7]=1.[C:27]([O:31][C:32]([N:34]1[CH2:39][CH:38]=[C:37](B2OC(C)(C)C(C)(C)O2)[CH2:36][CH2:35]1)=[O:33])([CH3:30])([CH3:29])[CH3:28].C(=O)([O-])[O-].[K+].[K+]>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].O1CCOCC1>[C:32]([N:34]1[CH2:35][CH:36]=[C:37]([C:2]2[CH:3]=[C:4]([CH:8]3[N:12]([C:13]4[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=4[Cl:19])[N:11]=[C:10]([C:20]([F:26])([F:25])[C:21]([F:22])([F:24])[F:23])[CH2:9]3)[CH:5]=[CH:6][CH:7]=2)[CH2:38][CH2:39]1)([O:31][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:33]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 4642098Tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine-1-carboxylateHCID 118431639HCID 118431639, compound

Product 1

HCID 118431798HCID 118431798, compoundYield 89.9%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
90 °C

Procedure

5-(3-Bromo-phenyl)-1-(2-chloro-phenyl)-3-pentafluoroethyl-4,5-dihydro-1H-pyrazole (1.0 g, 2.2 mmol) prepared in Step 1 of Preparation 6, 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,6-dihydro-2H-pyridin-1-carboxylic acid tert-butyl ester (820.0 mg, 2.6 mmol), Pd(dppf)Cl2 (181.0 mg, cat.) and potassium carbonate (915.0 mg, 6.6 mmol) were added to a mixed solvent of 1,4-dioxane (32.0 mL) and distilled water (8.0 mL). The reaction mixture was stirred at 90° C. for 12 hours and then filtered through celite pad. A saturated solution of ammonium chloride was added to the filtrate, which was then extracted with ethyl acetate three times. The combined extract washed with brine, dried on anhydrous magnesium sulfate, and then concentrated under reduced pressure to give a yellow liquid residue. The resulting residue was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/8) to give 1.1 g of the titled compound as a yellow liquid.

Workup

  1. distillationdistilled water (8.0 mL)
  2. filtrationfiltered through celite pad
  3. additionA saturated solution of ammonium chloride was added to the filtrate, which
  4. extractionwas then extracted with ethyl acetate three times
  5. extractionThe combined extract
  6. washwashed with brine
  7. dry with materialdried on anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customto give a yellow liquid residue
  10. customThe resulting residue was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/8)

Sources & evidence

ORD record
ord-1638c2af7ee8411aaec1b172e28bbc5a
Source dataset
uspto-grants-2016_06
Patent number
US09376420B2

Reaction notes

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