Cesium carbonate → methyl {[6-(1,5-diphenyl-1H-pyrrol-2-yl)-2-naphthyl]oxy}acetate

HRID 456841Notes

Reaction equation

[C:1]1([N:7]2[C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[CH:10][CH:9]=[C:8]2[C:18]2[CH:19]=[C:20]3[C:25](=[CH:26][CH:27]=2)[CH:24]=[C:23]([OH:28])[CH:22]=[CH:21]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:30][C:31]([O:33][CH3:34])=[O:32].C(=O)([O-])[O-].[Cs+].[Cs+]>>[C:1]1([N:7]2[C:11]([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)=[CH:10][CH:9]=[C:8]2[C:18]2[CH:19]=[C:20]3[C:25](=[CH:26][CH:27]=2)[CH:24]=[C:23]([O:28][CH2:30][C:31]([O:33][CH3:34])=[O:32])[CH:22]=[CH:21]3)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

Reactant 3

HCID 10796Cesium carbonate

HCID 60984Methyl bromoacetate

HCID 184390266-(1,5-diphenyl-1H-pyrrol-2-yl)-2-naphthol

Product 1

HCID 86603528methyl {[6-(1,5-diphenyl-1H-pyrrol-2-yl)-2-naphthyl]oxy}acetateYield 92%

Procedure

In a similar manner as described in step 6 of Example 1, the title compound was prepared from 6-(1,5-diphenyl-1H-pyrrol-2-yl)-2-naphthol (0.200 g, 0.553 mmol), prepared in step 2 of Example 11, methyl bromoacetate (0.102 g, 0.664 mmol) and cesium carbonate (0.900 g, 2.77 mmol) with the exception that the product was extracted with methylene chloride. Purification on a Biotage Horizon™ system with a KP-Sil Flash 40+M column (100 g Silica Gel, 60 Å) using 55% to 95% methylene chloride in hexane as the eluent gave methyl {[6-(1,5-diphenyl-1H-pyrrol-2-yl)-2-naphthyl]oxy}acetate as an off-white solid (0.22 g, 92%), mp 188–189° C. Elemental Analysis for C29H23NO3.0.16 CH2Cl2 Calc'd: C, 78.34; H, 5.26; N, 3.13. Found: C, 77.73; H, 5.08; N, 3.07.

Workup

extractionwas extracted with methylene chloride
customPurification on a Biotage Horizon™ system with a KP-Sil Flash 40+M column (100 g Silica Gel, 60 Å)

Sources & evidence

ORD record: ord-b4726ea5ec7249a1b87606720afb04f6
Source dataset: uspto-grants-2007_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07186749B2

Reaction notes

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