1,2-Dimethoxyethane → HCID 118432078, compound

HRID 2208081Notes

Reaction equation

HRID 2208081 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([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]([C:26]([F:29])([F:28])[F:27])([C:22]([F:25])([F:24])[F:23])[OH:21])[CH2:9]2)=[CH:4][C:3]=1[F:30].[C:31]([C:34]1[CH:35]=[C:36](B(O)O)[CH:37]=[CH:38][CH:39]=1)(=[O:33])[CH3:32].C(=O)([O-])[O-].[Na+].[Na+].COCCOC>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.C(OCC)(=O)C.C(O)C>[C:31]([C:34]1[CH:39]=[C:38]([C:2]2[CH:7]=[CH:6][C:5]([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]([C:22]([F:25])([F:24])[F:23])([C:26]([F:29])([F:28])[F:27])[OH:21])[CH2:9]3)=[CH:4][C:3]=2[F:30])[CH:37]=[CH:36][CH:35]=1)(=[O:33])[CH3:32]

Participants

8

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 27343103-Acetylphenylboronic acidHCID 118431944HCID 118431944, compound

Product 1

HCID 118432078HCID 118432078, compoundYield 16%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

5-(4-bromo-3-fluoro-phenyl)-1-(2-chloro-phenyl)-3-[di-(trifluoromethyl)-hydroxy-methyl]-4,5-dihydro-1H-pyrazole (30.0 mg, 0.056 mmol) prepared in Step 5 of Preparation 21, 3-acetylphenylboronic acid (10.4 mg, 0.064 mmol), Pd(PPh3)4 (6.7 mg, 0.006 mmol), and a 2N sodium carbonate solution (145.0 uL) were added to a mixed solvent of 1,2-dimethoxyethane (2.0 mL) and ethanol (0.5 mL). The reaction mixture was stirred at 90° C. for 3 hours and then ethyl acetate was added thereto. The reaction mixture was washed with distilled water and 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=1/5) to give 5.0 mg of the titled compound as a yellow liquid.

Workup

  1. washThe reaction mixture was washed with distilled water and brine
  2. dry with materialdried on anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customto give a yellow liquid residue
  5. customThe resulting residue was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/5)

Sources & evidence

ORD record
ord-0718225f0664426980eba13d2935ee9e
Source dataset
uspto-grants-2016_06
Patent number
US09376420B2

Reaction notes

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