Pyridine → HCID 54164588, compound

HRID 2296690Notes

Reaction equation

HRID 2296690 reaction equation
[NH2:1][C:2]1[C:7]([C:8]([OH:18])([C:13]#[C:14]C(C)C)[C:9]([F:12])([F:11])[F:10])=[CH:6][C:5]([F:19])=[CH:4][CH:3]=1.N1[CH:25]=[CH:24]C=CC=1.Br[CH2:27][C:28](Br)=[O:29].[CH3:31]COCC>>[F:19][C:5]1[CH:4]=[CH:3][C:2]2[N:1]([C:24]#[CH:25])[C:28](=[O:29])[CH2:27][O:18][C:8]([CH:13]([CH3:14])[CH3:31])([C:9]([F:10])([F:11])[F:12])[C:7]=2[CH:6]=1

Participants

5

Reactant 4

HCID 1049PyridineHCID 3283Diethyl Ether2×HCID 61147Bromoacetyl bromideHCID 69959296HCID 69959296, compound

Product 1

HCID 54164588HCID 54164588, compound

Procedure

To a stirred 0° solution of 210 mg of 6-Amino-3-fluoro-α-isopropylethynyl-α-(trifluoromethyl)benzyl alcohol in 20 mL of dry ether was added 0.120 mL of dry pyridine and 0.080 mL of bromoacetyl bromide. After 30 min, the reaction mixture was diluted with ether, washed with water and aqueous sodium bicarbonate, dried and evaporated. The residue was dissolved in 20 mL of dry DMF and was treated at room temperature with 33 mg of 100% sodium hydride for 30 min. The reaction was partitioned between ethyl acetate and water and the ethyl acetate layer was washed with brine, dried and evaporated. The crude product was purified by column chromatography over silica gel (elution with ethyl acetate/hexanes 1:2) affording after crystallization from ethyl acetate/hexanes 89 mg of the title compound as colorless crystals: mp 172-173°; Anal. Calcd. for C15H13NO2F4: C, 57.15; H, 4.17; N, 4.44. Found: C, 57.10; H, 3.98; N, 4.21.

Workup

  1. washwashed with water and aqueous sodium bicarbonate
  2. customdried
  3. customevaporated
  4. dissolutionThe residue was dissolved in 20 mL of dry DMF
  5. additionwas treated at room temperature with 33 mg of 100% sodium hydride for 30 min
  6. customThe reaction was partitioned between ethyl acetate and water
  7. washthe ethyl acetate layer was washed with brine
  8. customdried
  9. customevaporated
  10. customThe crude product was purified by column chromatography over silica gel (elution with ethyl acetate/hexanes 1:2)
  11. customaffording
  12. customafter crystallization from ethyl acetate/hexanes 89 mg of the title compound as colorless crystals

Sources & evidence

ORD record
ord-e8c7431f7380414fa4506eb9abcc0f74
Source dataset
uspto-grants-2002_12
Patent number
US06489320B1

Reaction notes

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