Nitrogen → HCID 19789709, compound

HRID 1614673Notes

Reaction equation

HRID 1614673 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([Sn](C)(C)C)=[CH:3][CH:2]=1.N#N.Br[C:15]1[C:19]([Br:20])=[CH:18][S:17][CH:16]=1.CCOC(C)=O>C1(C)C=CC=CC=1.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>[Br:20][C:19]1[C:15]([C:4]2[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=2)=[CH:16][S:17][CH:18]=1

Participants

7

Reactant 4

HCID 947NitrogenHCID 8857Ethyl AcetateHCID 184523,4-DibromothiopheneHCID 617834Stannane, trimethyl(4-methylphenyl)-

Product 1

HCID 19789709HCID 19789709, compoundYield 45%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent2×

Conditions

Temperature
120 °C

Procedure

Through a solution of p-tolyltrimethyltin (3.17 g, 12.4 mmol) in dry toluene (8 mL) was bubbled N2 for 5 min to degas the solution. To this was added 3,4-dibromothiophene (2.31 g, 9.56 mmol) and a catalytic amount of Pd(PPh3)4 (552 mg, 5 mol %). The reaction mixture was brought to reflux (120° C.) and left overnight. The reaction was cooled to rt and the toluene was replaced by EtOAc. The insoluable salts were removed by filtration through a plug of celite. The product was purified by flash chromatography on a silica column eluting with hexane to afford 1.09 g (45%) of the titled compound as a clear, colorless oil.

Workup

  1. customto degas the solution
  2. temperatureThe reaction was cooled to rt
  3. customThe insoluable salts were removed by filtration through a plug of celite
  4. customThe product was purified by flash chromatography on a silica column
  5. washeluting with hexane

Sources & evidence

ORD record
ord-fcf4867c37b84a21bdc5431445c70764
Source dataset
uspto-grants-1993_03
Patent number
US05198438

Reaction notes

Loading…