Cesium carbonate → methyl 3-phenyl-2-[(6-{5-phenyl-1-[4-(trifluoromethyl)benzyl]-1H-pyrrol-2-yl}-2-naphthyl)oxy]propanoate

HRID 456832Notes

Reaction equation

HRID 456832 reaction equation
[C:1]1([C:7]2[N:11]([CH2:12][C:13]3[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=3)[C:10]([C:23]3[CH:24]=[C:25]4[C:30](=[CH:31][CH:32]=3)[CH:29]=[C:28]([OH:33])[CH:27]=[CH:26]4)=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:34][O:35][C:36](=[O:53])[CH:37](OS(C(F)(F)F)(=O)=O)[CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>>[C:39]1([CH2:38][CH:37]([O:33][C:28]2[CH:27]=[CH:26][C:25]3[C:30](=[CH:31][CH:32]=[C:23]([C:10]4[N:11]([CH2:12][C:13]5[CH:14]=[CH:15][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:17][CH:18]=5)[C:7]([C:1]5[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=5)=[CH:8][CH:9]=4)[CH:24]=3)[CH:29]=2)[C:36]([O:35][CH3:34])=[O:53])[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1

Participants

4

Reactant 3

HCID 10796Cesium carbonateHCID 13388932alpha-(Trifluoromethylsulfonyloxy)hydrocinnamic acid methyl esterHCID 184390346-{5-phenyl-1-[4-(trifluoromethyl)benzyl]-1H-pyrrol-2-yl}-2-naphthol

Product 1

HCID 18439045methyl 3-phenyl-2-[(6-{5-phenyl-1-[4-(trifluoromethyl)benzyl]-1H-pyrrol-2-yl}-2-naphthyl)oxy]propanoateYield 90%

Procedure

In a similar manner as described in step 1 of Example 7, the title compound was prepared from 6-{5-phenyl-1-[4-(trifluoromethyl)benzyl]-1H-pyrrol-2-yl}-2-naphthol (0.300 g, 0.676 mmol), prepared in the previous step, 3-phenyl-2-trifluoromethanesulfonyloxypropionic acid methyl ester (0.317 g, 1.02 mmol) and cesium carbonate (0.441 g, 1.35 mmol). Purification on a Biotage Horizon™ system with a KP-Sil Flash 40+M column (100 g Silica Gel, 60 Å) using 25% to 65% methylene chloride in hexane as the eluent gave methyl 3-phenyl-2-[(6-{5-phenyl-1-[4-(trifluoromethyl)benzyl]-1H-pyrrol-2-yl}-2-naphthyl)oxy]propanoate as an off-white amorphous solid (0.367 g, 90%), mp 50–55° C. Elemental Analysis for C38H30F3NO3 Calc'd: C, 75.36; H, 4.99; N, 2.31. Found: C, 75.24; H, 5.16; N, 2.22.

Workup

  1. 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-8622357ff7e74e9b9c11c09f8b38d6df
Source dataset
uspto-grants-2007_03
Patent number
US07186749B2

Reaction notes

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