1-Naphthaleneboronic acid → HCID 22998404, compound

HRID 234463Notes

Reaction equation

HRID 234463 reaction equation
[C:1]1(B(O)O)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.Br[C:15]1[S:19][C:18]([S:20]([N:23]2[CH:27]=[CH:26][CH:25]=[CH:24]2)(=[O:22])=[O:21])=[CH:17][CH:16]=1>>[C:1]1([C:15]2[S:19][C:18]([S:20]([N:23]3[CH:27]=[CH:26][CH:25]=[CH:24]3)(=[O:21])=[O:22])=[CH:17][CH:16]=2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 2

HCID 2545321-Naphthaleneboronic acidHCID 23445587N-(5-bromothiophenesulfonyl)pyrrole

Product 1

HCID 22998404HCID 22998404, compoundYield 87%

Procedure

N-[5-(1-napthyl)thiophene-2-sulfonyl]pyrrole was prepared in the same manner as described in Example 32C from 1-napthaleneboronic acid (353 mg, 2.05 mmol) and N-(5-bromothiophene-2-sulfonyl)pyrrole (600 mg, 2.05 mmol). Purification by column chromatography using 2% ethyl acetate/hexanes gave the pure sulfonamide in 87% yield as a pale yellow clear oil.

Workup

  1. customPurification by column chromatography

Sources & evidence

ORD record
ord-cfc04ff72a7347e88fe9cb0fb32ab461
Source dataset
uspto-grants-1997_01
Patent number
US05594021

Reaction notes

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