2-bromo-N,N-diethylbenzenesulfonamide → 4'-(5-Aminopyrazin-2-yl)-N,N-diethyl-3'-fluorobiphenyl-2-sulfonamide

HRID 1523787Notes

Reaction equation

HRID 1523787 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[S:31]([N:34]([CH2:37][CH3:38])[CH2:35][CH3:36])(=[O:33])=[O:32]>>[NH2:23][C:20]1[N:21]=[CH:22][C:17]([C:3]2[CH:4]=[CH:5][C:6]([C:25]3[C:26]([S:31]([N:34]([CH2:37][CH3:38])[CH2:35][CH3:36])(=[O:32])=[O:33])=[CH:27][CH:28]=[CH:29][CH:30]=3)=[CH:7][C:2]=2[F:1])=[N:18][CH:19]=1

Participants

3

Reactant 2

HCID 263700292-bromo-N,N-diethylbenzenesulfonamideHCID 903122765-(2-Fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-phenyl)-pyrazin-2-amine

Product 1

HCID 778446414'-(5-Aminopyrazin-2-yl)-N,N-diethyl-3'-fluorobiphenyl-2-sulfonamide

Procedure

The title compound was prepared in a manner similar to that described in Example 448 using 5-(2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-pyrazin-2-amine and 2-bromo-N,N-diethylbenzenesulfonamide. MS (ESI): mass calcd. for C20H21FN4O2S, 400.14; m/z found, 401.2 [M+H]+. 1H NMR (400 MHz, CD3OD) δ 8.37 (s, 1H), 8.29 (d, J=1.4, 1H), 8.08-8.04 (m, 1H), 8.0-7.94 (m, 1H), 7.70-7.64 (m, 1H), 7.61-7.55 (m, 1H), 7.41-7.36 (m, 1H), 7.32-7.25 (m, 2H), 2.96 (q, J=7.1, 4H), 1.00 (t, J=7.1, 6H).

Sources & evidence

ORD record
ord-a1a97f54457c483a9d0ae53776f9f257
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

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