Pyridinium chloride → 6-(1-benzyl-5-phenyl-1H-pyrrol-2-yl)-2-naphthol

HRID 456817Notes

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:28]=[CH:27][C:26]2[C:21](=[CH:22][CH:23]=[C:24]([O:29]C)[CH:25]=2)[CH:20]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.N1C=CC=CC=1>>[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]([OH:29])[CH:23]=[CH:22]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Reactant 2

HCID 10176127Pyridinium chloride

HCID 184390211-benzyl-2-(6-methoxy-2-naphthyl)-5-phenyl-1H-pyrrole

Product 1

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

Conditions

Temperature: 180 °C

Procedure

In a similar manner as described in step 5 of Example 1, the title compound was prepared from 1-benzyl-2-(6-methoxy-2-naphthyl)-5-phenyl-1H-pyrrole (0.22 g, 0.56 mmol), prepared in the previous step, and pyridine hydrochloride (15 g) heated to 180° C. under nitrogen for 3 hours. Purification on a Biotage FlashElute™ system with a KP-Sil Flash 40+M column (90 g Silica Gel, 60 Å) using methylene chloride as the eluent gave 6-(1-benzyl-5-phenyl-1H-pyrrol-2-yl)-2-naphthol a grayish solid (0.155 g, 73%), mp 153–154° C. Elemental Analysis for C27H21NO Calc'd: C, 86.37; H, 5.64; N, 3.73. Found: C, 85.95; H, 5.86; N, 3.59.

Workup

customPurification on a Biotage FlashElute™ system with a KP-Sil Flash 40+M column (90 g Silica Gel, 60 Å)

Sources & evidence

ORD record: ord-965d844f99a543a5b4e2c5a79553cd6f
Source dataset: uspto-grants-2007_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07186749B2

Reaction notes

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