1-Bromo-2-(cyclopropylsulfonyl)benzene → 6-Amino-3-[2'-(cyclopropylsulfonyl)-3-fluorobiphenyl-4-yl]pyrazine-2-carbonitrile

HRID 1524131Notes

Reaction equation

HRID 1524131 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([C:8]#[N:9])[C:5]([C:10]2[CH:15]=[CH:14][C:13](B3OC(C)(C)C(C)(C)O3)=[CH:12][C:11]=2[F:25])=[N:4][CH:3]=1.Br[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[S:33]([CH:36]1[CH2:38][CH2:37]1)(=[O:35])=[O:34]>>[NH2:1][C:2]1[N:7]=[C:6]([C:8]#[N:9])[C:5]([C:10]2[CH:15]=[CH:14][C:13]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[S:33]([CH:36]3[CH2:38][CH2:37]3)(=[O:35])=[O:34])=[CH:12][C:11]=2[F:25])=[N:4][CH:3]=1

Participants

3

Reactant 2

HCID 681817441-Bromo-2-(cyclopropylsulfonyl)benzeneHCID 90312891HCID 90312891, compound

Product 1

HCID 903137136-Amino-3-[2'-(cyclopropylsulfonyl)-3-fluorobiphenyl-4-yl]pyrazine-2-carbonitrile

Procedure

The title compound was prepared using conditions analogous to those used to make Example 6 utilizing 6-amino-3-(2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrazine-2-carbonitrile and 1-bromo-2-(cyclopropylsulfonyl)benzene. MS (ESI): mass calcd. for C20H15FN4O2S, 394.09; m/z found, 395.0 [M+H]+. 1H NMR (600 MHz, DMSO-δ6) δ 8.26 (s, 1H), 8.07 (dd, J=8.0, 1.3, 1H), 7.82-7.77 (m, 1H), 7.74-7.69 (m, 1H), 7.66-7.62 (m, 1H), 7.52 (dd, J=7.6, 1.3, 1H), 7.44 (dd, J=10.8, 1.7, 1H), 7.41-7.36 (m, 3H), 2.47-2.41 (m, 1H), 0.99-0.91 (m, 2H), 0.90-0.83 (m, 2H).

Sources & evidence

ORD record
ord-8e8f932158724b6190c9a5e05fa6a88a
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

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