Iodoethane → Ethyl 2-isonicotinoylthiophene-3-carboxylate

HRID 920901Notes

Reaction equation

HRID 920901 reaction equation
[C:1]([C:9]1[S:10][CH:11]=[CH:12][C:13]=1[C:14]([OH:16])=[O:15])(=[O:8])[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].[CH3:23][CH2:24]I>CC#N>[C:1]([C:9]1[S:10][CH:11]=[CH:12][C:13]=1[C:14]([O:16][CH2:23][CH3:24])=[O:15])(=[O:8])[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 10796Cesium carbonateHCID 866831162-Isonicotinoylthiophene-3-carboxylic acid

Product 1

HCID 86683117Ethyl 2-isonicotinoylthiophene-3-carboxylateYield 85.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
30 °C

Procedure

To a solution of 2-isonicotinoylthiophene-3-carboxylic acid (2.2 g, 9.4 mmol) from example 2.1 and Cs2CO3 (6.2 g, 18.9 mmol) in CH3CN (500 mL) was added CH3CH2I (2.9 g, 18.9 mmol) dropwise. The mixture was stirred at 30° C. for 48 h. The mixture was filtered and concentrated to give the title compound as yellow oil (2.1 g, 85.5% yield).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-12aaae79a88842b49121054ed5447ce6
Source dataset
uspto-grants-2016_03
Patent number
US09273068B2

Reaction notes

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