(6-(2-Aminopyrimidin-5-yl)-5-fluoropyridin-3-yl)boronic acid → 2-[6-(2-Aminopyrimidin-5-yl)-5-fluoropyridin-3-yl]-N-ethyl-5-(trifluoromethyl)benzenesulfonamide

HRID 1524100Notes

Reaction equation

HRID 1524100 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[N:13]=[CH:12][C:11](B(O)O)=[CH:10][C:9]=2[F:17])=[CH:4][N:3]=1.Br[C:19]1[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][C:20]=1[S:29]([NH:32][CH2:33][CH3:34])(=[O:31])=[O:30]>>[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[N:13]=[CH:12][C:11]([C:19]3[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:26])[F:27])=[CH:21][C:20]=3[S:29]([NH:32][CH2:33][CH3:34])(=[O:31])=[O:30])=[CH:10][C:9]=2[F:17])=[CH:4][N:3]=1

Participants

3

Reactant 2

HCID 90313056(6-(2-Aminopyrimidin-5-yl)-5-fluoropyridin-3-yl)boronic acidHCID 903136902-Bromo-N-ethyl-5-(trifluoromethyl)benzenesulfonamide

Product 1

HCID 903143692-[6-(2-Aminopyrimidin-5-yl)-5-fluoropyridin-3-yl]-N-ethyl-5-(trifluoromethyl)benzenesulfonamide

Procedure

The title compound was prepared in a manner similar to that described in Example 427 using (6-(2-aminopyrimidin-5-yl)-5-fluoropyridin-3-yl)boronic acid and 2-bromo-N-ethyl-5-(trifluoromethyl)benzenesulfonamide. MS (ESI): mass calcd. for C18H15F4N5O2S, 441.09; m/z found, 442.0 [M+H]+. 1H NMR (400 MHz, CD3OD) δ 8.94 (d, J=1.1, 2H), 8.51-8.46 (m, 1H), 8.37-8.31 (m, 1H), 8.03 (dd, J=8.1, 1.9, 1H), 7.81 (dd, J=11.9, 1.8, 1H), 7.68 (d, J=7.9, 1H), 2.86 (q, J=7.3, 2H), 1.02 (t, J=7.2, 3H).

Sources & evidence

ORD record
ord-8faa369243814b0ab5796aeb5b0d8332
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

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