Sodium hydride → HCID 9920866, compound

HRID 1784344Notes

Reaction equation

HRID 1784344 reaction equation
F[C:2]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][C:3]=1[C:4]([OH:6])=O.C(N1C=CN=C1)(N1C=CN=C1)=O.[NH:24]1[CH2:28][CH2:27][CH2:26][C@@H:25]1[CH2:29][OH:30].[H-].[Na+]>CN(C)C=O.O>[F:11][C:8]1[CH:9]=[CH:10][C:2]2[O:30][CH2:29][C@H:25]3[CH2:26][CH2:27][CH2:28][N:24]3[C:4](=[O:6])[C:3]=2[CH:7]=1

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 682631,1'-CarbonyldiimidazoleHCID 763392,5-Difluorobenzoic acidHCID 2724541Prolinol, (R)-

Product 1

HCID 9920866HCID 9920866, compoundYield 20.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2,5-difluorobenzoic acid (1.0 g; 6.325 mmol) in dimethylformamide (5 ml) was added 1,1′- carbonyldiimidazole (1.07 g; 6.64 mmol) and the solution stirred at room temperature for 1 h, followed by the addition of (R)-(−)-2-pyrrolidinemethanol (0.655 ml; 6.64 mmol). The reaction was stirred at room temperature overnight whereupon 60% sodium hydride in mineral oil (0.507 g; 12.7 mmol) was carefully added and the mixture was heated to 120° C. for 2 h. The reaction was cautiously diluted with water and extracted with ethyl acetate and the organic layer washed with water then dried (Na2SO4) and evaporated to give the crude product. Trituration with ether and filtration afforded the title compound (0.29 g). M.p.: 85-86° C.; EIMS: m/z=222.2 [M+H]+

Workup

  1. additionwas carefully added
  2. temperaturethe mixture was heated to 120° C. for 2 h
  3. extractionextracted with ethyl acetate
  4. washthe organic layer washed with water
  5. dry with materialthen dried (Na2SO4)
  6. customevaporated
  7. customto give the crude product
  8. filtrationTrituration with ether and filtration

Sources & evidence

ORD record
ord-d0ce27d6184f4135ae882c06d881c0a7
Source dataset
uspto-grants-2009_03
Patent number
US07504390B2

Reaction notes

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