Dicyclohexylamine → Ethyl 5-(3,3-dimethylbut-1-yn-1-yl)-4-methylisoxazole-3-carboxylate

HRID 1478170Notes

Reaction equation

HRID 1478170 reaction equation
Br[C:2]1[O:6][N:5]=[C:4]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[C:3]=1[CH3:12].[CH3:13][C:14]([CH3:18])([CH3:17])[C:15]#[CH:16].C1(NC2CCCCC2)CCCCC1>C(#N)C.[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:13][C:14]([CH3:18])([CH3:17])[C:15]#[C:16][C:2]1[O:6][N:5]=[C:4]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[C:3]=1[CH3:12]

Participants

7

Reactant 3

HCID 7582DicyclohexylamineHCID 135123,3-Dimethyl-1-butyneHCID 58828802Ethyl 5-bromo-4-methyl-1,2-oxazole-3-carboxylate2×

Product 1

HCID 118511143Ethyl 5-(3,3-dimethylbut-1-yn-1-yl)-4-methylisoxazole-3-carboxylate

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
100 °C

Procedure

Ethyl 5-bromo-4-methylisoxazole-3-carboxylate (Intermediate A) (100 mg, 0.427 mmol) and 3,3-dimethylbut-1-yne (0.058 mL, 0.470 mmol) in acetonitrile (3 mL) were degassed thoroughly refilling with nitrogen. Dicyclohexylamine (0.085 mL, 0.427 mmol), CuI (2.85 mg, 0.015 mmol) and PdCl2(PPh3)2 (7.50 mg, 10.68 mmol) were added. The mixture was stirred in the microwave at 100° C. for 45 mins. The resulting mixture was adsorbed onto silica and purification by chromatography eluting with 0-10% EtOAc in iso-hexane afforded the title compound;

Workup

  1. customThe resulting mixture was adsorbed onto silica and purification by chromatography
  2. washeluting with 0-10% EtOAc in iso-hexane

Sources & evidence

ORD record
ord-5303c8d73467488787aa992bdcfd43de
Source dataset
uspto-grants-2016_08
Patent number
US09403810B2

Reaction notes

Loading…