Pyridine → HCID 56982471, compound

HRID 369740Notes

Reaction equation

HRID 369740 reaction equation
[NH2:1][C:2]1[C:7]([C:8]([OH:20])([C:13]#[C:14][C:15]2[O:16][CH:17]=[CH:18][CH:19]=2)[C:9]([F:12])([F:11])[F:10])=[CH:6][C:5]([Cl:21])=[CH:4][CH:3]=1.N1C=CC=CC=1.Br[CH2:29][CH2:30][C:31](Br)=[O:32]>CCOCC>[Cl:21][C:5]1[CH:4]=[CH:3][C:2]2[NH:1][C:31](=[O:32])[C@H:30]([CH3:29])[O:20][C@:8]([C:13]#[C:14][C:15]3[O:16][CH:17]=[CH:18][CH:19]=3)([C:9]([F:10])([F:11])[F:12])[C:7]=2[CH:6]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 10998423BromopropionylbromideHCID 54107311HCID 54107311, compound

Product 1

HCID 56982471HCID 56982471, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a stirred ice-cooled solution of 265 mg of 6-amino-3-chloro-α-(furan-2-yl)ethynyl-α-(trifluoromethyl)benzyl alcohol in 10 mL of dry ether was added 0.150 mL of dry pyridine and 0.100 mL of bromopropionyl 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 at 0°, 25 mg of 100% sodium hydride was added, and the resulting mixture was stirred for 15 min at 0° and at room temperature for 30 min. The reaction mixture was then poured onto water and extracted twice with ether. The combined extracts were washed with water and brine, dried and evaporated to a residue which was purified by column chromatography on silica gel (elution with 17-33% ethyl acetate in hexanes) affording after crystallization from ethyl acetale/hexanes 5 mg of the title compound: HRMS: Calcd. for C17H12NO3ClF3 (M+H)+ : 369.037956. Found: 369.036835.

Workup

  1. washwashed with water and aqueous sodium bicarbonate
  2. customdried
  3. customevaporated
  4. dissolutionThe residue was dissolved in 10 mL of dry DMF at 0°
  5. addition25 mg of 100% sodium hydride was added
  6. additionThe reaction mixture was then poured onto water
  7. extractionextracted twice with ether
  8. washThe combined extracts were washed with water and brine
  9. customdried
  10. customevaporated to a residue which
  11. customwas purified by column chromatography on silica gel (elution with 17-33% ethyl acetate in hexanes)
  12. customaffording
  13. customafter crystallization from ethyl acetale/hexanes 5 mg of the title compound

Sources & evidence

ORD record
ord-c15cf1e3c77c47bf924709cbe1c13110
Source dataset
uspto-grants-2000_10
Patent number
US06140320

Reaction notes

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