Water → N-(5-(5-formylfuran-2-yl)-4-methylthiazol-2-yl)acetamide

HRID 2386175Notes

Reaction equation

HRID 2386175 reaction equation
Br[C:2]1[S:6][C:5]([NH:7][C:8](=[O:10])[CH3:9])=[N:4][C:3]=1[CH3:11].[CH:12]([C:14]1[O:18][C:17](B(O)O)=[CH:16][CH:15]=1)=[O:13].C(=O)(O)[O-].[Na+].O>CN1C(=O)CCC1.[Pd](Cl)Cl>[CH:12]([C:14]1[O:18][C:17]([C:2]2[S:6][C:5]([NH:7][C:8](=[O:10])[CH3:9])=[N:4][C:3]=2[CH3:11])=[CH:16][CH:15]=1)=[O:13]

Participants

7

Reactant 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 822437N-(5-bromo-4-methyl-1,3-thiazol-2-yl)acetamideHCID 27343555-Formylfuran-2-boronic acid

Product 1

HCID 14532745N-(5-(5-formylfuran-2-yl)-4-methylthiazol-2-yl)acetamideYield 37.6%

Reagents, catalysts & solvents 2

HCID 24290Palladium ChlorideCatalystHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To a solution of 3.0 g of N-(5-bromo-4-methylthiazol-2-yl)acetamide in 50 mL of NMP was added 3.0 g of 5-formylfuran-2-ylboronic acid. To the stirred solution was then added 300 mg of 1,1 bis-(diphenylphosphino)-ferrocene) palladium dichloride followed by 10 mL of saturated sodium bicarbonate. The resulting biphasic mixture was irradiated at 150° C. in a microwave for 20 min. The resulting mixture was poured into 200 mL of water and filtered. The filtrate was extracted with ether and the ether layers were combined, dried over sodium sulfate and concentrated. The resulting oil was precipitated with methylene chloride and filtered, yielding 1.2 g of N-(5-(5-formylfuran-2-yl)-4-methylthiazol-2-yl)acetamide as an orange solid which was used without further purification. LC/MS: 251.07 (M+H)/2.18 min.

Workup

  1. customThe resulting biphasic mixture was irradiated at 150° C. in a microwave for 20 min
  2. filtrationfiltered
  3. extractionThe filtrate was extracted with ether
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customThe resulting oil was precipitated with methylene chloride
  7. filtrationfiltered

Sources & evidence

ORD record
ord-bd27cf2b1efd4a50a4358e2fa564ac30
Source dataset
uspto-grants-2012_09
Patent number
US08268818B2

Reaction notes

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