1,2-Dimethoxyethane → HCID 10409947, compound

HRID 732017Notes

Reaction equation

HRID 732017 reaction equation
I[C:2]1[CH:3]=[C:4]([C:8]2[O:12][N:11]=[C:10]([CH2:13][S:14][C:15]3[N:19]([CH3:20])[C:18]([C:21]4[S:22][CH:23]=[CH:24][CH:25]=4)=[N:17][N:16]=3)[N:9]=2)[CH:5]=[CH:6][CH:7]=1.[O:26]1[CH:30]=[CH:29][C:28](B(O)O)=[CH:27]1.COCCOC.C(=O)([O-])[O-].[Na+].[Na+]>C(OCC)(=O)C.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:26]1[CH:30]=[CH:29][C:28]([C:2]2[CH:3]=[C:4]([C:8]3[O:12][N:11]=[C:10]([CH2:13][S:14][C:15]4[N:19]([CH3:20])[C:18]([C:21]5[S:22][CH:23]=[CH:24][CH:25]=5)=[N:17][N:16]=4)[N:9]=3)[CH:5]=[CH:6][CH:7]=2)=[CH:27]1

Participants

7

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 2734358Furan-3-boronic acidHCID 10480329HCID 10480329, compound

Product 1

HCID 10409947HCID 10409947, compoundYield 59.3%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

To 5-(3-Iodo-phenyl)-3-(4-methyl-5-thiophen-2-yl-4H-[1,2,4]triazol-3-ylsulfanylmethyl)-[1,2,4]oxadiazole (50 mg, 0.10 mmol) in a vial was added 3-furan boronic acid (17 mg, 0.16 mmol), tetrakis(triphenylphosphine)palladium(0) (6 mg, 0.0052 mmol), ethylene glycol dimethyl ether (1 ml) and 2 M sodium carbonate (1 ml). The vial was then sealed and heated at 90° C. for 1 h with vigorous stirring. The reaction was cooled, diluted with ethyl acetate, washed with water and saturated brine, filtered and concentrated. The residue was purified by flash column chromatography using 70% ethyl acetate in hexanes. Additional purification by trituration with a mixture of diethyl ether and hexanes and then filtration afforded the title compound as a beige solid 25 mg (57%). 1H NMR (CDCI3), δ (ppm): 8.18 (s, 1H), 7.98 (d, 1H), 7.79 (s, 1H), 7.71 (d, 1H), 7.51 (m, 4H), 7.17 (m, 1H), 6.74 (s, 1H), 4.55 (s, 2H), 3.73 (s, 3H).

Workup

  1. customThe vial was then sealed
  2. temperatureThe reaction was cooled
  3. washwashed with water and saturated brine
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by flash column chromatography
  7. customAdditional purification by trituration
  8. additionwith a mixture of diethyl ether and hexanes
  9. filtrationfiltration

Sources & evidence

ORD record
ord-41146b68227641938c0c5b68c2737438
Source dataset
uspto-grants-2009_09
Patent number
US07585881B2

Reaction notes

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