Cesium carbonate → Methyl {[6-(1-benzyl-5-phenyl-1H-pyrrol-2-yl)-2-naphthyl]oxy}acetate

HRID 456827Notes

Reaction equation

[CH2:1]([N:8]1[C:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:11][CH:10]=[C:9]1[C:19]1[CH:20]=[C:21]2[C:26](=[CH:27][CH:28]=1)[CH:25]=[C:24]([OH:29])[CH:23]=[CH:22]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:31][C:32]([O:34][CH3:35])=[O:33].C(=O)([O-])[O-].[Cs+].[Cs+]>>[CH2:1]([N:8]1[C:12]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[CH:11][CH:10]=[C:9]1[C:19]1[CH:20]=[C:21]2[C:26](=[CH:27][CH:28]=1)[CH:25]=[C:24]([O:29][CH2:31][C:32]([O:34][CH3:35])=[O:33])[CH:23]=[CH:22]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Reactant 3

HCID 10796Cesium carbonate

HCID 60984Methyl bromoacetate

HCID 184390296-(1-benzyl-5-phenyl-1H-pyrrol-2-yl)-2-naphthol

Product 1

HCID 86603526Methyl {[6-(1-benzyl-5-phenyl-1H-pyrrol-2-yl)-2-naphthyl]oxy}acetate

Procedure

In a similar manner as described in step 1 of Example 4, the title compound was prepared from 6-(1-benzyl-5-phenyl-1H-pyrrol-2-yl)-2-naphthol (0.250 g, 0.665 mmol), prepared in step 2 of Example 2, methyl bromoacetate (0.122 g, 0.797 mmol) and cesium carbonate (1.08 g, 3.33 mmol). The isolated tan amorphous solid (0.298 g, 100%) was used without further purification, mp 101–102° C. Elemental Analysis for C30H25NO3 Calc'd: C, 80.51; H, 5.63; N, 3.13. Found: C, 79.81; H, 5.60; N, 2.83.

Workup

customThe isolated tan amorphous solid (0.298 g, 100%) was used without further purification, mp 101–102° C

Sources & evidence

ORD record: ord-ba849fb33628427f9b5363fba760b531
Source dataset: uspto-grants-2007_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07186749B2

Reaction notes

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