1-Bromo-2-(cyclopropylsulfonyl)benzene → 5-[2'-(Cyclopropylsulfonyl)-3-fluorobiphenyl-4-yl]pyrazin-2-amine

HRID 1523839Notes

Reaction equation

HRID 1523839 reaction equation
[F:1][C:2]1[CH:7]=[C:6](B2OC(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[S:31]([CH:34]1[CH2:36][CH2:35]1)(=[O:33])=[O:32]>>[CH:34]1([S:31]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=2[C:6]2[CH:5]=[CH:4][C:3]([C:17]3[N:18]=[CH:19][C:20]([NH2:23])=[N:21][CH:22]=3)=[C:2]([F:1])[CH:7]=2)(=[O:32])=[O:33])[CH2:36][CH2:35]1

Participants

3

Reactant 2

HCID 681817441-Bromo-2-(cyclopropylsulfonyl)benzeneHCID 903122765-(2-Fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-phenyl)-pyrazin-2-amine

Product 1

HCID 903125785-[2'-(Cyclopropylsulfonyl)-3-fluorobiphenyl-4-yl]pyrazin-2-amine

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-bromo-2-(cyclopropylsulfonyl)benzene. MS (ESI): mass calcd. for C19H16FN3O2S, 369.09; m/z found, 370.0 [M+H]+. 1H NMR (400 MHz, CD3OD) δ 8.55-8.49 (m, 1H), 8.33 (s, 1H), 8.13 (dd, J=8.0, 1.2, 1H), 8.11-8.05 (m, 1H), 7.77 (m, 1H), 7.68 (m, 1H), 7.48 (dd, J=7.6, 1.1, 1H), 7.43-7.36 (m, 2H), 2.35-2.26 (m, 1H), 1.04-0.91 (m, 4H).

Sources & evidence

ORD record
ord-877e20a4030548b6ae41f714a759d108
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

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