Iodoethane → HCID 89539133, compound

HRID 1498878Notes

Reaction equation

HRID 1498878 reaction equation
[CH2:1](I)[CH3:2].C([O-])([O-])=O.[Cs+].[Cs+].[Br:10][C:11]1[C:12]([C:24]([OH:26])=[O:25])=[C:13]([C:16](=[O:23])[C:17]2[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=2)[S:14][CH:15]=1>CC#N>[Br:10][C:11]1[C:12]([C:24]([O:26][CH2:1][CH3:2])=[O:25])=[C:13]([C:16](=[O:23])[C:17]2[CH:18]=[CH:19][N:20]=[CH:21][CH:22]=2)[S:14][CH:15]=1

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 10796Cesium carbonateHCID 717436084-Bromo-2-(pyridine-4-carbonyl)thiophene-3-carboxylic acid

Product 1

HCID 89539133HCID 89539133, compoundYield 25.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of ethyl iodide (3.78 mL, 48.06 mmol), Cs2CO3 (15.66 g, 48.06 mmol) and 4-bromo-2-isonicotinoylthiophene-3-carboxylic acid (5 g, 16.02 mmol) in CH3CN (150 mL) was stirred at room temperature for about 12 h in a 250 mL round-bottomed flask. After completion of the reaction, the solvent was removed under reduced pressure. The reaction mixture was diluted with water and the aqueous layer was back extracted with ethyl acetate (3×100 mL). The combined organic layers were dried with Na2SO4, filtered and concentrated to afford a yellow solution. The resulting mixture was deposited onto silica gel, loaded onto a silica gel column and eluted with 5:1 PE/EtOAc to give the title compound (1.37 g, 25% yield). LC-MS (Method A): m/z 340 (M+H)+, Rt: 1.07 min.

Workup

  1. customAfter completion of the reaction
  2. customthe solvent was removed under reduced pressure
  3. additionThe reaction mixture was diluted with water
  4. extractionthe aqueous layer was back extracted with ethyl acetate (3×100 mL)
  5. dry with materialThe combined organic layers were dried with Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto afford a yellow solution
  9. washeluted with 5:1 PE/EtOAc

Sources & evidence

ORD record
ord-773300a27da944a59b30b2ee1c2f903c
Source dataset
uspto-grants-2015_12
Patent number
US09200005B2

Reaction notes

Loading…