Patent ID: 7115746

Claim:
A process for producing a diaryl amine compound of the formula (I): or a salt thereof, said process comprising the steps of (1) coupling a compound of formula (II) with an amine of formula (III) in the presence of an alkali metal salt or a transition metal catalyst: to form a compound of formula (IV): and (2) removing radical Y from the compound of formula (IV) in the presence of an acid; wherein: Ar 1 and Ar 2 are independently Q; wherein each Q is an aryl or heteroaryl ring system optionally fused to a saturated or unsaturated 5–8 membered sing having 0–4 heteroatoms, wherein either Ar 1 or Ar 2 , is a heteroaryl ring; wherein Q is optionally substituted at one or more ring atoms with one or more substituents independently selected from halo; C 1 –C 6 aliphatic optionally substituted with N(R′) 2 , OR′, CO 2 R′, C(O)N(R′) 2 , OC(O)N(R′) 2 , NR′CO 2 R′, NR′C(O)R′, SO 2 N(R′) 2 , N═CH—N(R′) 2 , or OPO 3 H 2 ; C 1 –C 6 alkoxy optionally substituted with N(R′) 2 , OR′, CO 2 R′, C(O)N(R′) 2 , OC(O)N(R′) 2 , NR′CO 2 R′, NR′C(O)R′, SO 2 N(R′) 2 , N═CH—N(R′) 2 , or OPO 3 H 2 ; Ar 3 ; CF 3 ; OCF 3 ; OR′; SR′; SO 2 N(R′) 2 ; OSO 2 R′; SCF 3 ; NO 2 ; CN; N(R′) 2 ; CO 2 R′; CO 2 N(R′) 2 ; C(O)N(R′) 2 ; NR′C(O)R′; NR′CO 2 R′; NR′C(O)C(O)R′; NR′SO 2 R′; OC(O)R′; NR′C(O)R 2 ; NR′CO 2 R 2 ; NR′C(O)C(O)R 2 ; NR′C(O)N(R′) 2 ; OC(O)N(R′) 2 ; NR′SO 2 R 2 ; NR′R 2 ; N(R 2 ) 2 , OC(O)R 2 ; OPO 3 H 2 ; and N═CH—N(R′) 2 ; R′ is selected from hydrogen; C 1 –C 6 aliphatic; or a 5–6 membered carbocyclic or heterocyclic ring system optionally substituted with 1 to 3 substituents independently selected from halo, C 1 –C 6 alkoxy, cyano, nitro, amino, hydroxy, and C 1–C 6 aliphatic; R 2 is a C 1 –C 6 aliphatic optionally substituted with N(R′) 2 , OR′, CO 2 R′, C(O)N(R′) 2 or SO 2 N(R′) 2 ; or a carbocyclic or heterocyclic ring system optionally substituted with N(R′) 2 , OR′, CO 2 R′, C(O)N(R′) 2 or SO 2 N(R′) 2 ; wherein Ar 3 is an aryl or heteroaryl ring system optionally fused to a saturated or unsaturated 5–8 membered ring having 0–4 heteroatoms; wherein Ar 3 is optionally substituted at one or more ring atoms with one or more substituents independently selected from halo; C 1 –C 6 aliphatic optionally substituted with N(R′) 2 , OR′, CO 2 R′, C(O)N(R′) 2 , OC(O)N(R′) 2 , NR′CO 2 R′, NR′C(O)R′, SO 2 N(R′) 2 , N═C—N(R′) 2 , or OPO 3 H 2 ; C 1 –C 6 alkoxy optionally substituted with N(R′) 2 , OR′, CO 2 R′, C(O)N(R′) 2 , OC(O)N(R′) 2 , SO 2 N(R′) 2 , NR′CO 2 R, NR′C(O)R′, N═C—N(R′) 2 , or OPO 3 H 2 ; CF 3 ; OCF 3 ; OR′; SR′; SO 2 N(R′) 2 ; OSO 2 R′; SCF 3 ; NO 2 ; CN; N(R′) 2 ; CO 2 R′; CO 2 N(R′) 2 ; C(O)N(R′) 2 ; NR′C(O)R′; NR′CO 2 R′; NR′C(O)C(O)R′; NR′SO 2 R′; OC(O)R′; NR′C(O)R 2 ; NR′CO 2 R 2 ; NR′C(O)C(O)R 2 ; NR′C(O)N(R′) 2 ; OC(O)N(R′) 2 ; NR′SO 2 R 2 ; NR′R 2 ; N(R 2 ) 2 ; OC(O)R 2 ; OPO 3 H 2 ; and —N═C—N(R′) 2 ; X is a leaving group; Y is —C(O)—O-Z; and Z is C 1 –C 6 aliphatic, benzyl, Fmoc, —SO 2 R′or Q, provided that Q is not substituted with X or alkyne.