N-methyl-2-pyrrolidone → HCID 21707249, compound

HRID 1384188Notes

Reaction equation

HRID 1384188 reaction equation
[CH2:1]1[O:11][C:10]2[CH:9]=[CH:8][C:5]([CH:6]=[CH2:7])=[CH:4][C:3]=2[O:2]1.C(N([CH:18]([CH3:20])[CH3:19])CC)(C)C.C[N:22]1[CH2:26][CH2:25][CH2:24][C:23]1=O>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:11]1[C:10]2[CH:9]=[CH:8][C:5](/[CH:6]=[CH:7]/[C:4]3[CH:3]=[CH:10][CH:9]=[C:19]4[C:18]=3[CH:20]=[C:25]([C:26]#[N:22])[CH:24]=[CH:23]4)=[CH:4][C:3]=2[O:2][CH2:1]1

Participants

5

Reactant 3

HCID 13387N-methyl-2-pyrrolidoneHCID 81531DiisopropylethylamineHCID 1389861,3-Benzodioxole, 5-ethenyl-

Product 1

HCID 21707249HCID 21707249, compound

Reagents, catalysts & solvents 1

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

Procedure

Example 53B (75 mg, 0.243 mmol), PdCl2(dppf) (20 mg, 0.024 mmol), 3,4-methylenedioxystyrene (43 mg, 0.291 mmol) and diisopropylethylamine (0.170 mL, 0.97 mmol) in N-methylpyrrolidinone (2 mL) were stirred at 90° C. for 18 h, cooled to room temperature and chromatographed on silica gel with 20% ethyl acetate/hexanes to provide 46 mg of the title compound.

Workup

  1. customwere stirred at 90° C. for 18 h
  2. customchromatographed on silica gel with 20% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-194e3780db8d46e48daaa5657e0fd57a
Source dataset
uspto-grants-2001_07
Patent number
US06258822B1

Reaction notes

Loading…