Sodium hydride → HCID 68539591, compound

HRID 1931410Notes

Reaction equation

HRID 1931410 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:11]=[C:12]([OH:15])[S:13][CH:14]=2)=[CH:6][CH:5]=1.[C:16]([O:20][C:21](=[O:24])[CH2:22]Br)([CH3:19])([CH3:18])[CH3:17]>CN(C=O)C>[C:16]([O:20][C:21](=[O:24])[CH2:22][O:15][C:12]1[S:13][CH:14]=[C:10]([C:7]2[CH:6]=[CH:5][C:4]([F:3])=[CH:9][CH:8]=2)[N:11]=1)([CH3:19])([CH3:18])[CH3:17]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 79177tert-Butyl bromoacetateHCID 178517499HCID 178517499, compound

Product 1

HCID 68539591HCID 68539591, compoundYield 96.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

123 mg (2.82 mmol) of sodium hydride (55% in mineral oil) were added to 500 mg (2.56 mmol) of 4-(4-fluoro-phenyl)-thiazol-2-ol in 15 ml of DMF. After stirring at room temperature for 30 min, 549.6 mg (2.82 mmol) of bromoacetic acid tert-butyl ester were added, and the reaction mixture was stirred at room temperature for 2 h. After evaporation, water was added, and the mixture was extracted with ethyl acetate. The combined organic phases were dried and evaporated to give 762 mg of a mixture of title compound and N-alkylated product.

Workup

  1. stirringthe reaction mixture was stirred at room temperature for 2 h
  2. customAfter evaporation, water
  3. additionwas added
  4. extractionthe mixture was extracted with ethyl acetate
  5. customThe combined organic phases were dried
  6. customevaporated

Sources & evidence

ORD record
ord-beb139dd11b94e0b957800e6545926ba
Source dataset
uspto-grants-2012_05
Patent number
US08188291B2

Reaction notes

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