2,5-Hexanedione → Ethyl 5-(2,5-dimethyl-1H-pyrrol-1-YL)thiazole-4-carboxylate

HRID 1170901Notes

Reaction equation

HRID 1170901 reaction equation
[NH2:1][C:2]1[S:6][CH:5]=[N:4][C:3]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8].[CH3:12][C:13](=O)[CH2:14][CH2:15][C:16](=O)[CH3:17]>[O-]S(C(F)(F)F)(=O)=O.[Sc+3].[O-]S(C(F)(F)F)(=O)=O.[O-]S(C(F)(F)F)(=O)=O>[CH3:17][C:16]1[N:1]([C:2]2[S:6][CH:5]=[N:4][C:3]=2[C:7]([O:9][CH2:10][CH3:11])=[O:8])[C:13]([CH3:12])=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 80352,5-HexanedioneHCID 12620181Ethyl 5-amino-1,3-thiazole-4-carboxylate

Product 1

HCID 59553905Ethyl 5-(2,5-dimethyl-1H-pyrrol-1-YL)thiazole-4-carboxylate

Reagents, catalysts & solvents 1

HCID 2734571Scandium(III) triflateCatalyst

Conditions

Temperature
180 °C

Procedure

A mixture of ethyl 5-aminothiazole-4-carboxylate (91.3 mg, 0.53 mmol), scandium (III) triflate (2.61 mg, 0.005 mmol) and 2,5-hexanedione (1.5 mL) was heated up to 180° C. for 1 h by microwave. The reaction was then concentrated and purified with silica gel chromatography to give a tan solid of ethyl 5-(2,5-dimethyl-1H-pyrrol-1-yl)thiazole-4-carboxylate (104 mg). 1H NMR (400 MHz, CDCl3) δ 8.82 (s, 1H), 5.92 (s, 2H), 4.25 (q, 2H), 2.01 (s, 6H), 1.20 (t, 3H). MS m/z 251.3 (M+H)+.

Workup

  1. concentrationThe reaction was then concentrated
  2. custompurified with silica gel chromatography

Sources & evidence

ORD record
ord-53680c47cfc143a39f33107ee4207f63
Source dataset
uspto-grants-2010_11
Patent number
US07829572B2

Reaction notes

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