Pyridine → HCID 18387394, compound

HRID 369742Notes

Reaction equation

HRID 369742 reaction equation
[NH2:1][C:2]1[C:7]([C:8]([OH:18])([C:13]#[C:14][CH:15]([CH3:17])[CH3:16])[C:9]([F:12])([F:11])[F:10])=[C:6]([F:19])[C:5]([F:20])=[CH:4][CH:3]=1.N1C=CC=CC=1.Br[CH2:28][C:29](Br)=[O:30]>CCOCC>[F:19][C:6]1[C:7]2[C:8]([C:13]#[C:14][CH:15]([CH3:17])[CH3:16])([C:9]([F:10])([F:11])[F:12])[O:18][CH2:28][C:29](=[O:30])[NH:1][C:2]=2[CH:3]=[CH:4][C:5]=1[F:20]

Participants

5

Reactant 3

HCID 1049PyridineHCID 61147Bromoacetyl bromideHCID 543750216-Amino-2,3-difluoro-alpha-(isopropylethynyl)-alpha-(trifluoromethyl)benzyl alcohol

Product 1

HCID 18387394HCID 18387394, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a stirred ice-cooled soliution of 81 mg of 6-Amino-2,3-difluoro-α-(isopropylethynyl)-α-(trifluoromethyl)benzyl alcohol in 8 mL of dry ether was added 0.55 mL of dry pyridine and 0.032 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 10 mL of dry DMF and was treated at 0° with 10 mg of 100% sodium hydride for 20 min. The cooling bath was removed, and the reaction was allowed to proceed at ambient temperature for 1 h. The reaction was quenched with one drop of acetic acid and then the mixture was concentrated in vacuo. The residue was dissolved in ethyl acetate and this solution vas washed with water and brine, dried and evaporated to a solid which was crystallized from ethyl acetate/hexanes affording 28 mg of the title compound as colorless crystals: mp 192.5-193.5°; HRMS: Calcd. for C15H13NO2F5 (M+H)+ : 334.086645. Found: 334.084917.

Workup

  1. washwashed with water and aqueous sodium bicarbonate
  2. customdried
  3. customevaporated
  4. dissolutionThe residue was dissolved in 10 mL of dry DMF
  5. additionwas treated at 0° with 10 mg of 100% sodium hydride for 20 min
  6. customThe cooling bath was removed
  7. waitto proceed at ambient temperature for 1 h
  8. customThe reaction was quenched with one drop of acetic acid
  9. concentrationthe mixture was concentrated in vacuo
  10. dissolutionThe residue was dissolved in ethyl acetate
  11. washthis solution vas washed with water and brine
  12. customdried
  13. customevaporated to a solid which
  14. customwas crystallized from ethyl acetate/hexanes affording 28 mg of the title compound as colorless crystals

Sources & evidence

ORD record
ord-3430fb3b9f974004bdf52016cef54d99
Source dataset
uspto-grants-2000_10
Patent number
US06140320

Reaction notes

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