2-Methyl-3-butyn-2-ol → HCID 86748033, compound

HRID 1741621Notes

Reaction equation

HRID 1741621 reaction equation
Br[C:2]1[CH:3]=[N:4][C:5]([C:12]2[NH:13][C:14](=[O:21])[C:15]([CH:18]([CH3:20])[CH3:19])([CH3:17])[N:16]=2)=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].[OH:22][C:23]([CH3:27])([CH3:26])[C:24]#[CH:25].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(N(CC)CC)C>[OH:22][C:23]([CH3:27])([CH3:26])[C:24]#[C:25][C:2]1[CH:3]=[N:4][C:5]([C:12]2[NH:13][C:14](=[O:21])[C:15]([CH:18]([CH3:20])[CH3:19])([CH3:17])[N:16]=2)=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8]

Participants

5

Reactant 3

HCID 82582-Methyl-3-butyn-2-olHCID 11776TriphenylphosphineHCID 13250604HCID 13250604, compound

Product 1

HCID 86748033HCID 86748033, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A stirred mixture of 12.6 g of 5-bromo-2-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)nicotinic acid, methyl ester, 3.4 g of 3-hydroxy-3-methyl-1-butyne, 0.02 g of bis(triphenylphosphine)palladium(II)-chloride, 0.04 g of triphenylphosphine, and 0.02 g of cuprous iodide in 300 mL of dry triethylamine is heated at reflux for 72 hours. The reaction is then filtered hot through celite, and the filtering agent is washed with methylene chloride. The combined filtrates were concentrated in vacuo, and the residue is partitioned between dilute aqueous hydrochloric acid and methylene chloride. The organic phase is washed with brine, dried, concentrated in vacuo, and the residue is chromatographed on silica gel using ether-methylene chloride mixtures to afford the desired product, mp 142°-145°.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 72 hours
  3. filtrationThe reaction is then filtered hot through celite
  4. washthe filtering agent is washed with methylene chloride
  5. concentrationThe combined filtrates were concentrated in vacuo
  6. customthe residue is partitioned between dilute aqueous hydrochloric acid and methylene chloride
  7. washThe organic phase is washed with brine
  8. customdried
  9. concentrationconcentrated in vacuo
  10. customthe residue is chromatographed on silica gel

Sources & evidence

ORD record
ord-8f94773bd9ee4ce5acf33fa238654dc7
Source dataset
uspto-grants-1994_08
Patent number
US05334576

Reaction notes

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