Acetonitrile → Ethyl 5-(4-isopropylcyclohex-1-en-1-yl)-4-methylisoxazole-3-carboxylate

HRID 1478147Notes

Reaction equation

HRID 1478147 reaction equation
[CH:1]([CH:4]1[CH2:9][CH2:8][C:7](B2OC(C)(C)C(C)(C)O2)=[CH:6][CH2:5]1)([CH3:3])[CH3:2].Br[C:20]1[O:24][N:23]=[C:22]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[C:21]=1[CH3:30].C(=O)([O-])[O-].[K+].[K+].CC#N>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].O>[CH:1]([CH:4]1[CH2:9][CH2:8][C:7]([C:20]2[O:24][N:23]=[C:22]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[C:21]=2[CH3:30])=[CH:6][CH2:5]1)([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 58828802Ethyl 5-bromo-4-methyl-1,2-oxazole-3-carboxylate2×HCID 747885964,4,5,5-Tetramethyl-2-[4-(propan-2-yl)cyclohex-1-en-1-yl]-1,3,2-dioxaborolane

Product 1

HCID 118511103Ethyl 5-(4-isopropylcyclohex-1-en-1-yl)-4-methylisoxazole-3-carboxylate

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolvent

Procedure

To a 2-5 mL microwave vial was added [2-(4-isopropylcyclohex-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane] (282 mg, 1.127 mmol), ethyl 5-bromo-4-methylisoxazole-3-carboxylate (Intermediate A) (264 mg, 1.127 mmol), PdCl2(dppf) (82 mg, 0.113 mmol), potassium carbonate (467 mg, 3.38 mmol), MeCN (2 mL) and water (0.667 mL). The vial was evacuated with nitrogen, sealed and placed in the microwave at 80° C. for 1 hr. The resulting mixture was diluted with EtOAc and water and the layers were separated. The organics were dried over MgSO4, filtered and concentrated under reduced pressure to give a brown oil, crude. The crude material was adsorbed onto silica and purification by chromatography eluting with 0-10% EtOAc in iso-hexane afforded the title compound;

Workup

  1. customThe vial was evacuated with nitrogen
  2. customsealed
  3. additionThe resulting mixture was diluted with EtOAc and water
  4. customthe layers were separated
  5. dry with materialThe organics were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customto give a brown oil, crude
  9. customThe crude material was adsorbed onto silica and purification by chromatography
  10. washeluting with 0-10% EtOAc in iso-hexane

Sources & evidence

ORD record
ord-28c538f3dc884370bdfb32e692ef748a
Source dataset
uspto-grants-2016_08
Patent number
US09403810B2

Reaction notes

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