Reaction #321635

ord-0e663bcd674842af8dc3f8b9f5d55884

Reaction equation

OB(O)c1cc(C(F)(F)F)cc(C(F)(F)F)c1
3,5-bis(trifluoromethyl)benzeneboronic acid
O=S(=O)(c1ccc(Br)s1)n1cccc1
N-[5-bromothiophene-2-sulfonyl]pyrrole
→
O=S(=O)(c1ccc(-c2cc(C(F)(F)F)cc(C(F)(F)F)c2)s1)n1cccc1
N-{5-[3,5-bis(trifluoromethyl)phenyl]thiophene-2-sulfonyl}pyrrole
Yield 93.0%

Reactants

OB(O)c1cc(C(F)(F)F)cc(C(F)(F)F)c1
3,5-bis(trifluoromethyl)benzeneboronic 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-[3,5-bis(trifluoromethyl)phenyl]thiophene-2-sulfonyl}pyrrole was prepared in the same manner as described in Example 32C from 3,5-bis(trifluoromethyl)benzeneboronic acid (619 mg, 2.26 mmol) and N-[5-bromothiophene-2-sulfonyl]pyrrole (60 mg, 2.05 mmol). Purification by column chromatography using 2% ethyl acetate/hexanes gave the pure sulfonamide as a white solid in 93% yield.

Source

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