1,2-Dimethoxyethane → HCID 57835212, compound

HRID 1364425Notes

Reaction equation

HRID 1364425 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6](I)[C:3]=1[C:4]#[N:5].[S:11]1[CH:15]=[CH:14][C:13](B(O)O)=[CH:12]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.O>[F:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([C:13]2[CH:14]=[CH:15][S:11][CH:12]=2)[C:3]=1[C:4]#[N:5]

Participants

7

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 5227222-Fluoro-6-iodobenzonitrileHCID 581760Thiophene-3-boronic acid

Product 1

HCID 57835212HCID 57835212, compoundYield 36.5%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Procedure

In a dry round bottom flask were added 2-fluoro-6-iodobenzonitrile (500 mg; 2.02 mmol), 3-thiophene boronic acid (311 mg; 2.43 mmol), sodium carbonate (2.32 g; 21.86 mmol), tetrakis(triphenylphosphine)palladium(0) (77 mg; 0.07 mmol), DME (20 mL) and water (20 mL) and heated to reflux for 5 hours. The reaction mixture was cooled to room temperature and extracted with ethyl acetate (3×), washed with brine (1×) and water (1×). Organic layers were combined and dried over sodium sulfate and then filtered and solvent removed to yield crude material which was purified by column chromatography (4% ethyl acetate/hexane) to obtain 150 milligrams of 2-fluoro-6-thiophen-3-yl-benzonitrile.

Workup

  1. temperatureheated
  2. temperatureto reflux for 5 hours
  3. extractionextracted with ethyl acetate (3×)
  4. washwashed with brine (1×) and water (1×)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customsolvent removed
  8. customto yield crude material which
  9. customwas purified by column chromatography (4% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-38258d68bea7409285a521c7c948eb06
Source dataset
uspto-grants-2011_02
Patent number
US07888366B2

Reaction notes

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