1-Bromo-2-(cyclopropylsulfonyl)benzene → 3-Amino-6-[2'-(cyclopropylsulfonyl)-3-fluorobiphenyl-4-yl]pyrazine-2-carbonitrile
Reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([CH:11]1[CH2:13][CH2:12]1)(=[O:10])=[O:9].[NH2:14][C:15]1[C:16]([C:37]#[N:38])=[N:17][C:18]([C:21]2[CH:26]=[CH:25][C:24](B3OC(C)(C)C(C)(C)O3)=[CH:23][C:22]=2[F:36])=[CH:19][N:20]=1>>[NH2:14][C:15]1[C:16]([C:37]#[N:38])=[N:17][C:18]([C:21]2[CH:26]=[CH:25][C:24]([C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=3[S:8]([CH:11]3[CH2:13][CH2:12]3)(=[O:10])=[O:9])=[CH:23][C:22]=2[F:36])=[CH:19][N:20]=1Participants
3
Procedure
The title compound was prepared in manner similar to that described in Example 88 using 1-bromo-2-(cyclopropylsulfonyl)benzene and 3-amino-6-(2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrazine-2-carbonitrile. MS (ESI): mass calcd. for C20H15FN4O2S, 394.09; m/z found, 395.1 [M+H]+. 1H NMR (500 MHz, CDCl3) δ 8.84 (d, J=1.8, 1H), 8.14 (dd, J=8.0, 1.4, 1H), 8.01 (m, 1H), 7.66 (m, 1H), 7.58 (m, 1H), 7.39-7.35 (m, 3H), 5.34 (s, 2H), 2.13-2.05 (m, 1H), 1.13-1.06 (m, 2H), 0.88-0.82 (m, 2H).
Sources & evidence
- ORD record
- ord-912985b2fa76454f831d45f2a29a646b
- Source dataset
- uspto-grants-2015_07
- Patent number
- US09079866B2
Reaction notes
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