Piperidine → HCID 58805189, compound

HRID 349703Notes

Reaction equation

HRID 349703 reaction equation
[OH:1][C:2]1[CH:11]=[C:10](OS(C(F)(F)F)(=O)=O)[CH:9]=[C:8]2[C:3]=1[C:4](=[O:26])[CH:5]=[C:6]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[O:7]2.[NH:27]1[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1.C1(C2C=CC=CC=2)C=CC=CC=1P(C(C)(C)C)C(C)(C)C.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C1COCC1.[Pd].[Pd].C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1>[OH:1][C:2]1[CH:11]=[C:10]([N:27]2[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]2)[CH:9]=[C:8]2[C:3]=1[C:4](=[O:26])[CH:5]=[C:6]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[O:7]2

Participants

7

Reactant 4

HCID 8082PiperidineHCID 62657Potassium Phosphate, TribasicHCID 27342152-(Di-tert-butylphosphino)biphenylHCID 11090323HCID 11090323, compound

Product 1

HCID 58805189HCID 58805189, compoundYield 17%

Reagents, catalysts & solvents 2

HCID 9832798Tris(dibenzylideneacetone) dipalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of trifluoromethanesulfonic acid 5-hydroxy-4-oxo-2-phenyl-4H-chromen-7-yl ester (130 mg, 0.337 mmol), piperidine (0.040 mL, 0.40 mmol), tris(dibenzylideneacetone) dipalladium(0) (15 mg, 0.017 mmol), biphenyl-2-yl-di-tert-butyl-phosphane (20 mg, 0.067 mmol), and tripotassium phosphate (K3PO4) (143 mg, 0.674 mmol) in THF (2 mL) was heated to reflux for 24 h, then cooled to room temperature for 24 h. The reaction mixture was filtered through a ¾″ silica gel (60 Å) plug. The plug was washed with EtOAc (75 mL), and the filtrate concentrated. The concentrate was purified via Biotage chromatography eluting with 5% EtOAc/hexanes to yield 18 mg (17%) of 5-hydroxy-2-phenyl-7-piperidin-1-yl-chromen-4-one.

Workup

  1. temperatureto reflux for 24 h
  2. filtrationThe reaction mixture was filtered through a ¾″ silica gel (60 Å) plug
  3. washThe plug was washed with EtOAc (75 mL)
  4. concentrationthe filtrate concentrated
  5. customThe concentrate was purified via Biotage chromatography
  6. washeluting with 5% EtOAc/hexanes

Sources & evidence

ORD record
ord-f38fc225d9ad4b5a86431a9bd3a237c0
Source dataset
uspto-grants-2007_02
Patent number
US07179912B2

Reaction notes

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