1-(2-Bromophenyl)-N-methylmethanesulfonamide → 1-[4'-(5-Aminopyrazin-2-yl)-3'-fluorobiphenyl-2-yl]-N-methylmethanesulfonamide formic acid salt

HRID 1523851Notes

Reaction equation

HRID 1523851 reaction equation
[F:1][C:2]1[CH:7]=[C:6](B2[O:12][C:11](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[CH2:31][S:32]([NH:35][CH3:36])(=[O:34])=[O:33]>>[CH:11]([OH:12])=[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[CH2:31][S:32]([NH:35][CH3:36])(=[O:33])=[O:34])=[CH:7][C:2]=2[F:1])=[N:18][CH:19]=1

Participants

3

Reactant 2

HCID 143717641-(2-Bromophenyl)-N-methylmethanesulfonamideHCID 903122765-(2-Fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-phenyl)-pyrazin-2-amine

Product 1

HCID 903140361-[4'-(5-Aminopyrazin-2-yl)-3'-fluorobiphenyl-2-yl]-N-methylmethanesulfonamide formic acid salt

Procedure

The title compound was prepared using analogous conditions to those described in Example 1 utilizing 5-(2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrazin-2-amine and 1-(2-bromophenyl)-N-methylmethanesulfonamide. MS (ESI): mass calcd. for C18H17FN4O2S, 372.11; m/z found, 373.1 [M+H]+. 1H NMR (400 MHz, CD3OD) δ 8.34 (s, 1H), 8.25 (s, 1H), 7.99 (m, 1H), 7.68-7.60 (m, 1H), 7.50-7.40 (m, 2H), 7.39-7.31 (m, 3H), 4.36 (s, 2H), 2.49 (s, 3H).

Sources & evidence

ORD record
ord-99237292f079488f8a0bc786f627c8b9
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

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