Water → HCID 2740601, compound

HRID 656846Notes

Reaction equation

HRID 656846 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1B(O)O.Cl[C:10]1[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][N:11]=1.C(=O)([O-])[O-].[K+].[K+].O>C(COC)OC>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:10]1[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][N:11]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 923422-Chloro-5-(trifluoromethyl)pyridineHCID 27339602-Thiopheneboronic acid

Product 1

HCID 2740601HCID 2740601, compoundYield 290.5%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

2-thienylboronic acid (Lancaster Synthesis, Inc., 1.00 g, 7.81 mmol), 2-chloro-5-trifluoromethylpyrdine (Adrich Chemical Co., 1.417 g, 7.81 mmol), tetrakistriphenylphosphine palladium(0) (Aldrich, 451 mg, 0.391 mmol), potassium carbonate (EM Science, 3.24 g, 23.4 mmol), water (20 mL), and dimethoxyethane (Aldrich, 20 mL) were allowed to stir at reflux for 20 hours under N2, after which time the mixture was cooled to room temperature and the organic and aqueous layers were separated. The aqueous layer was extracted with 3×50 mL of diethyl ether, and the combined organic fractions were dried with sodium sulfate, filtered, and the filtrate was evaporated to dryness. The crude product was purified by silica gel flash chromatography with CH2Cl2/hexanes (1:1) as the eluent (product Rf=0.5), to afford the product as a white crystalline solid (yield=5.2 g, 73% isolated yield). 1H NMR (CDCl3, 296 K, 300 MHz): δ=7.73-7.57 (2H, m), 7.55 (1H, d, J=8.5 Hz), 7.34 (1H, d, J=4.8 Hz), 6.88 (1H, d, J=4.8 Hz) ppm. 19F NMR (CDCl3, 296 K, 282 MHz) δ=−62.78 ppm. Intermediate bridged dimer,

Workup

  1. temperatureat reflux for 20 hours under N2
  2. customthe organic and aqueous layers were separated
  3. extractionThe aqueous layer was extracted with 3×50 mL of diethyl ether
  4. dry with materialthe combined organic fractions were dried with sodium sulfate
  5. filtrationfiltered
  6. customthe filtrate was evaporated to dryness
  7. customThe crude product was purified by silica gel flash chromatography with CH2Cl2/hexanes (1:1) as the eluent (product Rf=0.5)

Sources & evidence

ORD record
ord-44a62858bc0b418da070263276386136
Source dataset
uspto-grants-2011_12
Patent number
US08071975B2

Reaction notes

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