Pyridinium chloride → 6-{5-phenyl-1-[4-(trifluoromethyl)benzyl]-1H-pyrrol-2-yl}-2-naphthol

HRID 456831Notes

Reaction equation

C[O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([C:13]1[N:14]([CH2:24][C:25]3[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][CH:26]=3)[C:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:16][CH:17]=1)[CH:7]=[CH:6]2.Cl.N1C=CC=CC=1>>[C:18]1([C:15]2[N:14]([CH2:24][C:25]3[CH:26]=[CH:27][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:29][CH:30]=3)[C:13]([C:8]3[CH:9]=[C:10]4[C:5](=[CH:6][CH:7]=3)[CH:4]=[C:3]([OH:2])[CH:12]=[CH:11]4)=[CH:17][CH:16]=2)[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

Reactant 2

HCID 10176127Pyridinium chloride

HCID 184390242-(6-methoxy-2-naphthyl)-5-phenyl-1-[4-(trifluoromethyl)benzyl]-1H-pyrrole

Product 1

HCID 184390346-{5-phenyl-1-[4-(trifluoromethyl)benzyl]-1H-pyrrol-2-yl}-2-naphtholYield 78.2%

Conditions

Temperature: 165 °C

Procedure

In a similar manner as described in step 5 of Example 1, the title compound was prepared from 2-(6-methoxy-2-naphthyl)-5-phenyl-1-[4-(trifluoromethyl)benzyl]-1H-pyrrole (0.70 g, 1.5 mmol), prepared in the previous step, and pyridine hydrochloride (7 g) heated to 165° C. under nitrogen for 12 hours. Purification on a Biotage Horizon™ system with a KP-Sil Flash 40+M column (100 g Silica Gel, 60 Å) using 50% to 90% methylene chloride in hexane as the eluent gave 6-{5-phenyl-1-[4-(trifluoromethyl)benzyl]-1H-pyrrol-2-yl}-2-naphthol as a reddish-brown amorphous solid (0.52 g, 77%), mp 63–66° C. Elemental Analysis for C28H20F3NO Calc'd: C, 75.84; H, 4.55; N, 3.16. Found: C, 75.18; H, 4.41; N, 3.13.

Workup

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-dfeebf2fd5984f38aa87edbfb7d63334
Source dataset: uspto-grants-2007_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07186749B2

Reaction notes

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