Pyridine → HCID 5327777, compound

HRID 369734Notes

Reaction equation

HRID 369734 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:16]([NH:19][C:20](C2C=CC=CC=2)(C2C=CC=CC=2)[C:21]2[CH:26]=CC=CC=2)=[CH:17][CH:18]=1)[C:5]([OH:15])([C:10]#[C:11][CH:12]1[CH2:14][CH2:13]1)[C:6]([F:9])([F:8])[F:7].N1C=CC=CC=1.BrCCC(Br)=[O:49]>CCOCC>[Cl:1][C:2]1[CH:18]=[CH:17][C:16]2[NH:19][C:20](=[O:49])[C@H:21]([CH3:26])[O:15][C@:5](/[CH:10]=[CH:11]/[CH:12]3[CH2:14][CH2:13]3)([C:6]([F:9])([F:8])[F:7])[C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 10998423BromopropionylbromideHCID 15363077HCID 15363077, compound

Product 1

HCID 5327777HCID 5327777, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a stirred ice-cooled solition of 291 mg of trans-6-Amino-3-chloro-α-cyclopropylethenyl-α-(trifluoromethyl)benzyl alcohol (from Example 5, Part C.) in 13 mL of dry ether was added 0.180 mL of dry pyridine and 0.120 mL of bromopropionyl bromide. After 1 h, 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 40 mg of 100% sodium hydride. After 15 min the cooliing bath was removed and stirring was continued at ambient temperature for 20 h. The reaction was poured onto aqueous ammonium chloride and extracted with ether. The ether layer was washed with brine, dried and evaporated. The residie was dissolved in a small amount of ethyl acetate, and addition of hexane resulted in the crystallization of 40 mg of the title compound as colorless crystals: mp 171-172°; HRMS: Calcd. for C16H16NO2ClF3 (M+H)+ : 346.082166. Found: 346.080681. A second crop of slightly less pure product weighed 41 mg.

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 40 mg of 100% sodium hydride
  6. customAfter 15 min the cooliing bath was removed
  7. waitwas continued at ambient temperature for 20 h
  8. additionThe reaction was poured onto aqueous ammonium chloride
  9. extractionextracted with ether
  10. washThe ether layer was washed with brine
  11. customdried
  12. customevaporated
  13. dissolutionThe residie was dissolved in a small amount of ethyl acetate, and addition of hexane

Sources & evidence

ORD record
ord-889f69e4452f4e8b91fdc777958ee970
Source dataset
uspto-grants-2000_10
Patent number
US06140320

Reaction notes

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