Reaction #321645

ord-cfc04ff72a7347e88fe9cb0fb32ab461

Reaction equation

OB(O)c1cccc2ccccc12
1-napthaleneboronic acid
O=S(=O)(c1ccc(Br)s1)n1cccc1
N-(5-bromothiophene-2-sulfonyl)pyrrole
→
O=S(=O)(c1ccc(-c2cccc3ccccc23)s1)n1cccc1
N-[5-(1-napthyl)thiophene-2-sulfonyl]pyrrole
Yield 87.0%

Reactants

OB(O)c1cccc2ccccc12
1-napthaleneboronic acid
O=S(=O)(c1ccc(Br)s1)n1cccc1
N-(5-bromothiophene-2-sulfonyl)pyrrole

Reagents

None

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    OtherPurification by column chromatography

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.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05594021uspto-grants-1997_01