US 7,321,061 B2 | ||
Processes for the preparation of aryl- and heteroaryl-alkylsulfonyl halides | ||
Ronald S. Michalak, Congers, N.Y. (US); Mousumi Ghosh, Elmwood Park, N.J. (US); and Mahmut Levent, Bloomfield, N.J. (US) | ||
Assigned to Wyeth, Madison, N.J. (US) | ||
Filed on Feb. 23, 2005, as Appl. No. 11/64,241. | ||
Claims priority of provisional application 60/547600, filed on Feb. 25, 2004. | ||
Prior Publication US 2005/0187408 A1, Aug. 25, 2005 | ||
Int. Cl. C07C 309/00 (2006.01) |
U.S. Cl. 562—828 | 29 Claims |
1. A process for preparing a compound of Formula I:
Ar—R—SO2—X I
wherein:
Ar is aryl or heteroaryl optionally substituted by one or more substituents selected from the group consisting of halogen,
C1-C6 alkyl, C3-C7 cycloalkyl, heterocycloalkyl, formyl, cyano, nitro, OH, C1-C6 alkoxy, arylalkyloxy, C1-C6 haloalkyl, C1-C3 perhaloalkyl, C1-C6 haloalkoxy, C1-C3 perhaloalkoxy, NR1R2, NR1COR3, aryl, aryloxy, heteroaryl and heteroaryloxy;
R is C1-C6 alkylenyl;
R1 and R2 are each independently selected from the group consisting of H, C1-C6 alkyl and C3-C7 cycloalkyl; or R1 and R2 together with the N atom to which they are attached form a 5- or 6-membered heterocycle;
R3 is selected from the group consisting of H, C1-C6 alkyl and C3-C7 cycloalkyl; and
X is halogen; comprising:
(a) reacting a compound of Formula II:
Ar—R-L II wherein L is a leaving group, with a Group I or II metal sulfite salt optionally in the presence of a phase transfer catalyst
to form a sulfonic acid salt compound of Formula III:
(Ar—R—SO3−1)qM III
wherein M is a Group I or II metal ion;
wherein q is 1 where M is Group I metal ion, and q is 2 where M is a Group II metal ion;
(b) reacting said compound of Formula III with a protic acid to form a sulfonic acid compound of Formula IV:
Ar—R—SO3H IV
and
(c) reacting said compound of Formula IV with a halogen substitution reagent to form said compound of Formula I.
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