Pyridine → HCID 5327772, compound

HRID 369733Notes

Reaction equation

HRID 369733 reaction equation
[NH2:1][C:2]1[C:7]([C:8]([OH:17])([C:13]#[C:14][CH2:15][CH3:16])[C:9]([F:12])([F:11])[F:10])=[CH:6][C:5]([Cl:18])=[CH:4][CH:3]=1.N1C=CC=CC=1.Br[CH2:26][C:27](Br)=[O:28]>CCOCC>[C:13]([C:8]1([C:9]([F:10])([F:11])[F:12])[C:7]2[CH:6]=[C:5]([Cl:18])[CH:4]=[CH:3][C:2]=2[NH:1][C:27](=[O:28])[CH2:26][O:17]1)#[C:14][CH2:15][CH3:16]

Participants

5

Reactant 3

HCID 1049PyridineHCID 61147Bromoacetyl bromideHCID 54298240HCID 54298240, compound

Product 1

HCID 5327772HCID 5327772, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a stirred ice-cooled solition of 167 mg of 6-amino-3-chloro-α-(1-butynyl)-α-(trifluoromethyl)benzyl alcohol in 15 mL of dry ether was added 0.100 mL of dry pyridine and 0.066 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 15 mL of dry DMF and was treated at room temperature with 25 mg of 100% sodium hydride for 1.5 h. The reaction was partitioned between ethyl acetate and water and the ethyl acetate layer was washed with brine, dried and evaporated. The crude product wes purified by preparative silica gel TLC. (elution with ethel acetate/hexanes 1:2) affording after crystallization from ethyl acetate/hexanes 106 mg of the title compound as colorless crystals: mp 167 -168°; Anal. Calcd. for C14H11NO2ClF3 : C, 52.93; H, 3.49; N, 4.42. Found: C, 52.73; H, 3.64; N, 4.13.

Workup

  1. washwashed with water and aqueous sodium bicarbonate
  2. customdried
  3. customevaporated
  4. dissolutionThe residue was dissolved in 15 mL of dry DMF
  5. additionwas treated at room temperature with 25 mg of 100% sodium hydride for 1.5 h
  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 wes purified by preparative silica gel TLC
  11. wash(elution with ethel acetate/hexanes 1:2)
  12. customaffording
  13. customafter crystallization from ethyl acetate/hexanes 106 mg of the title compound as colorless crystals

Sources & evidence

ORD record
ord-a9b1b29d5470425490c630886c7737f5
Source dataset
uspto-grants-2000_10
Patent number
US06140320

Reaction notes

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