Cesium carbonate → methyl 3-phenyl-2-{[6-(5-phenyl-1H-pyrrol-2-yl)-2-naphthyl]oxy}propanoate

HRID 456814Notes

Reaction equation

HRID 456814 reaction equation
[C:1]1([C:7]2[NH:11][C:10]([C:12]3[CH:13]=[C:14]4[C:19](=[CH:20][CH:21]=3)[CH:18]=[C:17]([OH:22])[CH:16]=[CH:15]4)=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:23][O:24][C:25](=[O:42])[CH:26](OS(C(F)(F)F)(=O)=O)[CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CC(C)=O>[C:28]1([CH2:27][CH:26]([O:22][C:17]2[CH:16]=[CH:15][C:14]3[C:19](=[CH:20][CH:21]=[C:12]([C:10]4[NH:11][C:7]([C:1]5[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=5)=[CH:8][CH:9]=4)[CH:13]=3)[CH:18]=2)[C:25]([O:24][CH3:23])=[O:42])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 13388932alpha-(Trifluoromethylsulfonyloxy)hydrocinnamic acid methyl esterHCID 184390376-(5-phenyl-1H-pyrrol-2-yl)-2-naphthol

Product 1

HCID 18439046methyl 3-phenyl-2-{[6-(5-phenyl-1H-pyrrol-2-yl)-2-naphthyl]oxy}propanoateYield 95.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 6-(5-phenyl-1H-pyrrol-2-yl)-2-naphthol (0.300 g, 1.05 mmol), prepared in the previous step, 3-phenyl-2-trifluoromethanesulfonyloxypropionic acid methyl ester (0.492 g, 1.58 mmol) and cesium carbonate (0.685 g, 2.10 mmol) in acetone (50 mL) was stirred under nitrogen at ambient temperature overnight. The acetone was removed under reduced pressure and the residue partitioned between EtOAc and water. The layers were separated and the aqueous layer was extracted two times with EtOAc. The combined extracts were dried (MgSO4), filtered and the solvent removed under reduced pressure. Purification on a Biotage FlashElute™ system with a KP-Sil Flash 40L column (120 g Silica Gel, 60 Å) using 25% to 60% methylene chloride in hexane as the eluent gave methyl 3-phenyl-2-{[6-(5-phenyl-1H-pyrrol-2-yl)-2-naphthyl]oxy}propanoate as a grayish solid (0.447 g, 95%), mp 140–141° C. Elemental Analysis for C30H25NO3 Calc'd: C, 80.51; H, 5.63; N, 3.13. Found: C, 80.26; H, 5.70; N, 2.94.

Workup

  1. customThe acetone was removed under reduced pressure
  2. customthe residue partitioned between EtOAc and water
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted two times with EtOAc
  5. dry with materialThe combined extracts were dried (MgSO4)
  6. filtrationfiltered
  7. customthe solvent removed under reduced pressure
  8. customPurification on a Biotage FlashElute™ system with a KP-Sil Flash 40L column (120 g Silica Gel, 60 Å)

Sources & evidence

ORD record
ord-28bc9a1f5685414d8b3facbf5ede4050
Source dataset
uspto-grants-2007_03
Patent number
US07186749B2

Reaction notes

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