5-(2-Fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-phenyl)-pyrazin-2-amine → 5-{2'-[(4,4-Difluoropiperidin-1-yl)sulfonyl]-3-fluorobiphenyl-4-yl}pyrazin-2-amine

HRID 1523789Notes

Reaction equation

HRID 1523789 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]([N:34]1[CH2:39][CH2:38][C:37]([F:41])([F:40])[CH2:36][CH2:35]1)(=[O:33])=[O:32]>>[F:41][C:37]1([F:40])[CH2:38][CH2:39][N:34]([S:31]([C:26]2[CH:25]=[CH:30][CH:29]=[CH:28][C:27]=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:33])=[O:32])[CH2:35][CH2:36]1

Participants

3

Reactant 2

HCID 903122765-(2-Fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-phenyl)-pyrazin-2-amineHCID 903129081-((2-Bromophenyl)sulfonyl)-4,4-difluoropiperidine

Product 1

HCID 778441885-{2'-[(4,4-Difluoropiperidin-1-yl)sulfonyl]-3-fluorobiphenyl-4-yl}pyrazin-2-amine

Procedure

The title compound was prepared in a manner similar to that described in Example 448 using 5-(2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-pyrazin-2-amine and 1-((2-bromophenyl)sulfonyl)-4,4-difluoropiperidine. MS (ESI): mass calcd. for C21H19F3N4O2S, 448.12; m/z found, 449.2 [M+H]+. 1H NMR (400 MHz, CD3OD) δ 8.35 (s, 1H), 8.27 (d, J=1.4, 1H), 8.12 (d, J=8.0, 1H), 7.98 (m, 1H), 7.75-7.67 (m, 1H), 7.63 (m, 1H), 7.43 (d, J=7.6, 1H), 7.32 (d, J=10.6, 2H), 3.02-2.93 (m, 4H), 1.90-1.73 (m, 4H).

Sources & evidence

ORD record
ord-caba6ac930fc4bc186e95ad949e0e9ee
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

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