6-Amino-3-bromopyridine-2-carbonitrile → 4'-(6-Amino-2-cyanopyridin-3-yl)-N-(tert-butyl)-3'-fluoro-[1,1'-biphenyl]-2-sulfonamide
Reaction equation
[C:1]([NH:5][S:6]([C:9]1[C:10]([C:15]2[CH:20]=[CH:19][C:18](B3OC(C)(C)C(C)(C)O3)=[C:17]([F:30])[CH:16]=2)=[CH:11][CH:12]=[CH:13][CH:14]=1)(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:31][C:32]1[N:37]=[C:36]([C:38]#[N:39])[C:35](Br)=[CH:34][CH:33]=1>>[NH2:31][C:32]1[N:37]=[C:36]([C:38]#[N:39])[C:35]([C:18]2[CH:19]=[CH:20][C:15]([C:10]3[C:9]([S:6]([NH:5][C:1]([CH3:2])([CH3:3])[CH3:4])(=[O:7])=[O:8])=[CH:14][CH:13]=[CH:12][CH:11]=3)=[CH:16][C:17]=2[F:30])=[CH:34][CH:33]=1Participants
3
Procedure
The title compound was prepared using analogous conditions to those described in Example 6 utilizing N-(tert-butyl)-3′-fluoro-4′-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1′-biphenyl]-2-sulfonamide and 6-amino-3-bromo-2-cyanopyridine. MS (ESI): mass calcd. for C22H21FN4O2S, 424.14; m/z found, 424.9 [M+H]+. 1H NMR (500 MHz, DMSO-d6) δ 8.11-8.04 (d, J=7.9, 1H), 7.71-7.64 (m, 1H), 7.64-7.58 (m, 2H), 7.54-7.48 (m, 1H), 7.45-7.36 (dd, J=19.2, 9.2, 2H), 7.36-7.30 (dd, J=7.9, 1.6, 1H), 6.89-6.83 (d, J=8.7, 1H), 6.83-6.75 (d, J=10.0, 3H), 1.03 (s, 9H).
Sources & evidence
- ORD record
- ord-8f9a2b5fb1434d3aa2ccd71a2a447219
- Source dataset
- uspto-grants-2015_07
- Patent number
- US09079866B2
Reaction notes
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