Formamide → 5-Oxazol-4-yl-thiophene-3-carboxylic acid methyl ester

HRID 1914569

Reaction equation

HRID 1914569 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:9]=[C:8]([C:10](=O)[CH2:11]Br)[S:7][CH:6]=1)=[O:4].[CH:14]([NH2:16])=[O:15]>>[CH3:1][O:2][C:3]([C:5]1[CH:9]=[C:8]([C:10]2[N:16]=[CH:14][O:15][CH:11]=2)[S:7][CH:6]=1)=[O:4]

Participants

3

Reactant 2

HCID 713FormamideHCID 539045465-(2-Bromo-acetyl)-thiophene-3-carboxylic acid methyl ester

Product 1

HCID 581102445-Oxazol-4-yl-thiophene-3-carboxylic acid methyl ester

Conditions

Temperature
170 °C

Procedure

5-(2-Bromo-acetyl)-thiophene-3-carboxylic acid methyl ester (0.4 g, 1.52 mmol) was dissolved in formamide (2 mL) and the tube purged with nitrogen and then sealed. The mixture was heated at 170° C. for 20 minutes. The resultant solution was diluted with HCl (1 M) and water and washed with ethyl acetate. The organic phase was evaporated then purified by chromatography on a silica II cartridge, eluting with 2:1 pentane:DCM to neat DCM, to give the side product, 5-oxazol-4-yl-thiophene-3-carboxylic acid methyl ester as white solid (0.049 g). LCMS m/z 251.35 [M+MeCN+H]+ R. T.=3.07 min (Analytical Method 6).

Workup

  1. customthe tube purged with nitrogen
  2. customsealed
  3. additionThe resultant solution was diluted with HCl (1 M) and water
  4. washwashed with ethyl acetate
  5. customThe organic phase was evaporated
  6. customthen purified by chromatography on a silica II cartridge
  7. washeluting with 2:1 pentane

Sources & evidence

ORD record
ord-b807fab4938e4987a356bb06be0a6677
Source dataset
uspto-grants-2013_12
Patent number
US08614209B2

Linked notes

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