1,2-Dimethoxyethane → HCID 118431858, compound

HRID 2208095Notes

Reaction equation

HRID 2208095 reaction equation
Br[C:2]1[S:6][C:5]([CH:7]2[N:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[Cl:18])[N:10]=[C:9]([C:19]([C:25]([F:28])([F:27])[F:26])([C:21]([F:24])([F:23])[F:22])[OH:20])[CH2:8]2)=[CH:4][CH:3]=1.[CH3:29][S:30][C:31]1[CH:32]=[C:33](B(O)O)[CH:34]=[CH:35][CH:36]=1.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>[Cl:18][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[N:11]1[CH:7]([C:5]2[S:6][C:2]([C:35]3[CH:34]=[CH:33][CH:32]=[C:31]([S:30][CH3:29])[CH:36]=3)=[CH:3][CH:4]=2)[CH2:8][C:9]([C:19]([C:21]([F:22])([F:24])[F:23])([C:25]([F:27])([F:26])[F:28])[OH:20])=[N:10]1

Participants

8

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 27343833-(Methylthio)benzeneboronic acidHCID 118431912HCID 118431912, compound

Product 1

HCID 118431858HCID 118431858, compoundYield 8.3%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
88 °C

Procedure

5-(5-Bromo-thiophen-2-yl)-1-(2-chloro-phenyl)-3-[di-(trifluoromethyl)-hydroxy-methyl]-4,5-dihydro-1H-pyrazole (100.0 mg, 0.20 mmol) prepared in Step 5 of Preparation 23, 3-methylthiophenylboronic acid (50.4 mg, 0.30 mmol), Pd(PPh3)4 (23.0 mg, 0.02 mmol), and a 2N sodium carbonate solution (1.0 mL) were added to a mixed solvent of 1,2-dimethoxyethane (2.0 mL) and ethanol (1.0 mL). The reaction mixture was stirred at 88° C. for 4 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 9.2 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-8ad919389ad149e893bed3a799ebb290
Source dataset
uspto-grants-2016_06
Patent number
US09376420B2

Reaction notes

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