1,2-Dimethoxyethane → ethyl 1-[(4-phenyl-1,3-thiazol-2-yl)methyl]-1H-pyrazole-4-carboxylate

HRID 1257339Notes

Reaction equation

HRID 1257339 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]2[N:9]=[C:10]([CH2:13][N:14]3[CH:18]=[C:17]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH:16]=[N:15]3)[S:11][CH:12]=2)[CH:5]=[CH:6][CH:7]=1.C1(/C=C/B(O)O)C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+].C(COC)OC>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.O>[C:4]1([C:8]2[N:9]=[C:10]([CH2:13][N:14]3[CH:18]=[C:17]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH:16]=[N:15]3)[S:11][CH:12]=2)[CH:5]=[CH:6][CH:7]=[CH:2][CH:3]=1

Participants

7

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 11430Potassium CarbonateHCID 5702628Styrylboronic acidHCID 58127935ethyl 1-{[4-(3-bromophenyl)-1,3-thiazol-2-yl]methyl}-1H-pyrazole-4-carboxylate

Product 1

HCID 58127603ethyl 1-[(4-phenyl-1,3-thiazol-2-yl)methyl]-1H-pyrazole-4-carboxylateYield 15.3%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent2×

Conditions

Temperature
150 °C

Procedure

Under an argon atmosphere, a mixture of the compound (400 mg, 1.02 mmol) obtained in Example 27a, [(E)-2-phenylethenyl]boronic acid (200 mg, 1.33 mmol), tetrakistriphenylphosphinepalladium (118 mg, 0.10 mmol), potassium carbonate (282 mg, 2.04 mmol), dimethoxyethane (5 mL) and water (1 mL) was stirred under microwave conditions at 150° C. for 10 min. The mixture was allowed to cool to room temperature, water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained crude product was purified by column chromatography (hexane-hexane/ethyl acetate=70/30) to give a compound (49 mg, 12%) shown in Example 27b as a pale-yellow oil and a compound (85 mg, 27%) shown in Example 27c as a pale-red oil.

Workup

  1. temperatureto cool to room temperature
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe obtained organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe obtained crude product
  7. customwas purified by column chromatography (hexane-hexane/ethyl acetate=70/30)

Sources & evidence

ORD record
ord-d777fdd2ad474f279df3981efb948100
Source dataset
uspto-grants-2013_06
Patent number
US08461348B2

Reaction notes

Loading…