Diisopropylethylamine → HCID 22495561, compound

HRID 1815881Notes

Reaction equation

HRID 1815881 reaction equation
Br[C:2]1[C:10]2[O:9][CH:8]=[CH:7][C:6]=2[CH:5]=[C:4]([F:11])[CH:3]=1.[CH2:12]([N:19]1[CH2:23][CH:22]=[CH:21][CH2:20]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(N(CC)C(C)C)(C)C.[Li+].[Cl-].O1C=CC=C1P(C1OC=CC=1)C1OC=CC=1>CN(C)C=O.C(OCC)C.C([O-])(=O)C.C([O-])(=O)C.[Pd+2]>[CH2:12]([N:19]1[CH2:23][CH2:22][CH:21]([C:2]2[C:10]3[O:9][CH:8]=[CH:7][C:6]=3[CH:5]=[C:4]([F:11])[CH:3]=2)[CH2:20]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

9

Reactant 5

HCID 81531DiisopropylethylamineHCID 433294Lithium ChlorideHCID 521585Tris(furan-2-yl)phosphaneHCID 5615061-Benzyl-2,5-dihydropyrroleHCID 221448167-Bromo-5-fluoro-1-benzofuran

Product 1

HCID 22495561HCID 22495561, compoundYield 19%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 0.675 g (3.14 mMol) 7-bromo-5-fluorobenzofuran, 5.0 g (31.40 mMol)1-benzyl-3-pyrroline, 2.19 mL (12.56 mMol), N,N-diisopropylethylamine, 0.399 g (9.42 mMol) LiCl, 0.154 g (0.66 mMol) tri-2-furylphosphine, and 0.070 g (0.314 mMol) palladium diacetate in 10 mL N,N-dimethylformamide was heated under nitrogen at 100° C. for 48 hours. The mixture was diluted with 10 mL diethyl ether and filtered through celite. The filtrate was concentrated under reduced pressure and the oily residue was submitted to kugelrohr distillation to remove most of the pyrrole and pyrrolidine side-products. Flash chromatography of the residue (Et3N/Et2O/hexane 1:39:60) yielded 1-benzyl-3-(5-fluorobenzofur-7-yl)pyrrolidine (173 mg, 19%) as a colorless oil.

Workup

  1. filtrationfiltered through celite
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. distillationdistillation
  4. customto remove most of the pyrrole and pyrrolidine side-products

Sources & evidence

ORD record
ord-bc782ba3ff6e45f88225f7d78eca2e70
Source dataset
uspto-grants-2005_04
Patent number
US06881733B1

Reaction notes

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