Water → 2-(7-Hydroxy-2-oxo-2H-chromen-3-yl)-4-methyl-thiazole-5-carboxylic acid tert-butyl ester

HRID 579439Notes

Reaction equation

HRID 579439 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([C:13](=[S:15])[NH2:14])[C:8](=[O:12])[O:9]2)=[CH:4][CH:3]=1.[H-].[Na+].[C:18]([O:22][C:23](=[O:29])[CH:24](Br)[C:25](=O)[CH3:26])([CH3:21])([CH3:20])[CH3:19].O>CN(C)C=O>[C:18]([O:22][C:23]([C:24]1[S:15][C:13]([C:7]2[C:8](=[O:12])[O:9][C:10]3[C:5]([CH:6]=2)=[CH:4][CH:3]=[C:2]([OH:1])[CH:11]=3)=[N:14][C:25]=1[CH3:26])=[O:29])([CH3:21])([CH3:20])[CH3:19]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 108899382-Bromo-3-oxobutyric acid tert-butyl esterHCID 1355028867-hydroxy-2-oxo-2H-chromene-3-carbothioamide

Product 1

HCID 1363877692-(7-Hydroxy-2-oxo-2H-chromen-3-yl)-4-methyl-thiazole-5-carboxylic acid tert-butyl esterYield 62.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

To a suspension of 7-hydroxy-2-oxo-2H-chromene-3-carbothioic acid amide (221 mg, 1.0 mmol) in anhydrous N,N-dimethylformamide (5 mL) stirred at 0° C., sodium hydride (60% in oil, 44 mg, 1.1 mmol) was added portionwise. During addition a clear solution was formed with moderate effervescence. After 10 min, a solution of 2-bromo-3-oxo butyric acid tert-butyl ester (474 mg, 2.0 mmol) in anhydrous N,N-dimethylformamide (2 mL) was added dropwise and the mixture was stirred at room temperature for 16 h. The reaction was poured into water (20 mL) and extracted with chloroform (3×10 mL). The combined organic extracts were washed with water (3×5 mL), dried over MgSO4 and concentrated. The residue was triturated with diethyl ether, the solid product was collected and washed with diethyl ether. The title compound (224 mg, 0.623 mmol, 62.3%) was obtained as a yellow solid.

Workup

  1. additionDuring addition a clear solution
  2. customwas formed with moderate effervescence
  3. stirringthe mixture was stirred at room temperature for 16 h
  4. extractionextracted with chloroform (3×10 mL)
  5. washThe combined organic extracts were washed with water (3×5 mL)
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated
  8. customThe residue was triturated with diethyl ether
  9. customthe solid product was collected
  10. washwashed with diethyl ether

Sources & evidence

ORD record
ord-37403bd2f0ad4cbd84bd4858d4b28712
Source dataset
uspto-grants-2015_05
Patent number
US09040714B2

Reaction notes

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