2-(Morpholinosulfonyl)phenylboronic acid → 5-[3-Fluoro-2'-(morpholin-4-ylsulfonyl)biphenyl-4-yl]pyrazin-2-amine

HRID 1523784Notes

Reaction equation

HRID 1523784 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[CH:10][C:11]([NH2:14])=[N:12][CH:13]=2)=[C:4]([F:15])[CH:3]=1.[O:16]1[CH2:21][CH2:20][N:19]([S:22]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2B(O)O)(=[O:24])=[O:23])[CH2:18][CH2:17]1>>[F:15][C:4]1[CH:3]=[C:2]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=2[S:22]([N:19]2[CH2:20][CH2:21][O:16][CH2:17][CH2:18]2)(=[O:23])=[O:24])[CH:7]=[CH:6][C:5]=1[C:8]1[N:9]=[CH:10][C:11]([NH2:14])=[N:12][CH:13]=1

Participants

3

Reactant 2

HCID 441186322-(Morpholinosulfonyl)phenylboronic acidHCID 903128885-(4-Bromo-2-fluorophenyl)pyrazin-2-amine

Product 1

HCID 778441305-[3-Fluoro-2'-(morpholin-4-ylsulfonyl)biphenyl-4-yl]pyrazin-2-amine

Procedure

The title compound was prepared in a manner similar to that described in Example 42 using 5-(4-bromo-2-fluorophenyl)pyrazin-2-amine and (2-(morpholinosulfonyl)phenyl)boronic acid. MS (ESI): mass calcd. for C20H19FN4O3S, 414.12; m/z found, 415.2 [M+H]+. 1H NMR (400 MHz, CD3OD) δ 8.38 (s, 1H), 8.31 (s, 1H), 8.13-8.09 (m, 1H), 7.99 (m, 1H), 7.75-7.69 (m, 1H), 7.65-7.60 (m, 1H), 7.46-7.43 (m, 1H), 7.37-7.31 (m, 2H), 3.54-3.46 (m, 4H), 2.91-2.84 (m, 4H).

Sources & evidence

ORD record
ord-31029504d35f4442b8ae335afd9390fd
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

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