N-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)isobutylsulfonamide → N-[3'-Fluoro-4'-(5H-pyrrolo[2,3-b]pyrazin-2-yl)biphenyl-2-yl]-2-methylpropane-1-sulfonamide

HRID 1523996Notes

Reaction equation

HRID 1523996 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[NH:15][S:16]([CH2:19][CH:20]([CH3:22])[CH3:21])(=[O:18])=[O:17])O1.Br[C:25]1[CH:30]=[CH:29][C:28]([C:31]2[N:32]=[C:33]3[CH:39]=[CH:38][NH:37][C:34]3=[N:35][CH:36]=2)=[C:27]([F:40])[CH:26]=1>>[F:40][C:27]1[CH:26]=[C:25]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[NH:15][S:16]([CH2:19][CH:20]([CH3:21])[CH3:22])(=[O:17])=[O:18])[CH:30]=[CH:29][C:28]=1[C:31]1[N:32]=[C:33]2[CH:39]=[CH:38][NH:37][C:34]2=[N:35][CH:36]=1

Participants

3

Reactant 2

HCID 90312701N-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)isobutylsulfonamideHCID 90313071HCID 90313071, compound

Product 1

HCID 90313602N-[3'-Fluoro-4'-(5H-pyrrolo[2,3-b]pyrazin-2-yl)biphenyl-2-yl]-2-methylpropane-1-sulfonamide

Procedure

The title compound was prepared using methods analogous to those described in Step C of Example 490 using N-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)isobutylsulfonamide and 2-(4-bromo-2-fluorophenyl)-5H-pyrrolo[2,3-b]pyrazine. MS (ESI): mass calcd. C22H21FN4O2S, 424.14; m/z found, 425.1 [M+H]+. 1H NMR (400 MHz, CDCl3) δ 9.09 (s, 1H), 8.78 (d, J=2.6, 1H), 8.20-8.11 (m, 1H), 7.73-7.65 (m, 2H), 7.46-7.37 (m, 1H), 7.34-7.29 (m, 2H), 7.26-7.19 (m, 2H), 6.87-6.79 (m, 1H), 6.59 (s, 1H), 2.97 (d, J=6.6, 2H), 2.31-2.13 (m, 1H), 1.05 (d, J=6.7, 6H).

Sources & evidence

ORD record
ord-583faf8da6e045969bb439b0d9cd1928
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

Loading…