Iodoethane → Ethyl 2-isonicotinoylthiophene-3-carboxylate

HRID 1498885Notes

Reaction equation

HRID 1498885 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 (2.1 g, 85.5% yield) as yellow oil. LC-MS (Method A): m/z 340 (M+H)+, Rt: 0.81 min.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-b52c70d465e6462fb1f79944b0275241
Source dataset
uspto-grants-2015_12
Patent number
US09200005B2

Reaction notes

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