N-(2-bromophenyl)ethanesulfonamide → N-[4'-(5-Aminopyrazin-2-yl)-3'-fluorobiphenyl-2-yl]ethanesulfonamide

HRID 1523780Notes

Reaction equation

HRID 1523780 reaction equation
[F:1][C:2]1[CH:7]=[C:6](B2OC(C)(C)C(C)(C)O2)[CH:5]=[CH:4][C:3]=1[C:17]1[N:18]=[CH:19][C:20]([NH2:23])=[N:21][CH:22]=1.Br[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[NH:31][S:32]([CH2:35][CH3:36])(=[O:34])=[O:33]>>[NH2:23][C:20]1[N:21]=[CH:22][C:17]([C:3]2[CH:4]=[CH:5][C:6]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[NH:31][S:32]([CH2:35][CH3:36])(=[O:34])=[O:33])=[CH:7][C:2]=2[F:1])=[N:18][CH:19]=1

Participants

3

Reactant 2

HCID 3362983N-(2-bromophenyl)ethanesulfonamideHCID 903122765-(2-Fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-phenyl)-pyrazin-2-amine

Product 1

HCID 77844068N-[4'-(5-Aminopyrazin-2-yl)-3'-fluorobiphenyl-2-yl]ethanesulfonamide

Procedure

The title compound was prepared using analogous conditions to those described in Example 34 utilizing 5-(2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-pyrazin-2-amine and N-(2-bromophenyl)ethanesulfonamide. MS (ESI): mass calcd. for C18H17FN4O2S, 372.11; m/z found, 372.9 [M+H]+. 1H NMR (400 MHz, DMSO-d6) δ 9.08 (s, 1H), 8.43-8.36 (m, 1H), 8.04 (d, J=1.0, 1H), 7.93 (m, 1H), 7.46-7.28 (m, 6H), 6.72 (s, 2H), 2.91 (q, J=7.4, 2H), 1.07 (t, J=7.3, 3H).

Sources & evidence

ORD record
ord-64b5d62600134de1bca08407a3569087
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

Loading…