5-(Methylsulphonyl)pyridine-3-boronic acid → 4-Fluoro-1-(2-fluoro-5-(5-(methylsulfonyl)pyridin-3-yl)phenyl)-1-(2-methylpyridin-4-yl)-1H-isoindol-3-amine

HRID 1662226Notes

Reaction equation

HRID 1662226 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([F:26])=[C:6]([C:8]2([C:19]3[CH:24]=[CH:23][N:22]=[C:21]([CH3:25])[CH:20]=3)[C:16]3[C:11](=[C:12]([F:17])[CH:13]=[CH:14][CH:15]=3)[C:10]([NH2:18])=[N:9]2)[CH:7]=1.[CH3:27][S:28]([C:31]1[CH:32]=[C:33](B(O)O)[CH:34]=[N:35][CH:36]=1)(=[O:30])=[O:29]>>[F:17][C:12]1[CH:13]=[CH:14][CH:15]=[C:16]2[C:11]=1[C:10]([NH2:18])=[N:9][C:8]2([C:6]1[CH:7]=[C:2]([C:33]2[CH:34]=[N:35][CH:36]=[C:31]([S:28]([CH3:27])(=[O:30])=[O:29])[CH:32]=2)[CH:3]=[CH:4][C:5]=1[F:26])[C:19]1[CH:24]=[CH:23][N:22]=[C:21]([CH3:25])[CH:20]=1

Participants

3

Reactant 2

HCID 441193815-(Methylsulphonyl)pyridine-3-boronic acidHCID 585794991-(5-Bromo-2-fluorophenyl)-4-fluoro-1-(2-methylpyridin-4-yl)-1H-isoindol-3-amine

Product 1

HCID 462056384-Fluoro-1-(2-fluoro-5-(5-(methylsulfonyl)pyridin-3-yl)phenyl)-1-(2-methylpyridin-4-yl)-1H-isoindol-3-amineYield 32%

Procedure

The title compound was synthesized as described for Example 1 in 32% yield, starting from 1-(5-bromo-2-fluorophenyl)-4-fluoro-1-(2-methylpyridin-4-yl)-1H-isoindol-3-amine (80 mg, 0.19 mmol) and 5-(methylsulfonyl)pyridin-3-ylboronic acid (50.5 mg, 0.25 mmol). 1H NMR (500 MHz, DMSO-d6, 298 K) δ ppm 9.07 (d, 1 H), 9.04 (d, 1 H), 8.39 (t, 1 H), 8.31 (d, 1 H), 7.84 (m, 1 H), 7.62-7.69 (m, 2 H), 7.56 (m, 1 H), 7.38 (dd, 1 H), 7.28-7.34 (m, 1 H), 7.04 (s, 1 H), 6.98 (dd, 1 H), 6.76 (br. s., 2 H), 3.37 (s, 3 H), 2.38 (s, 3 H); MS (ES+) m/z 491 (M+1).

Sources & evidence

ORD record
ord-02c28f8dbc484102a453f889125ee0f1
Source dataset
uspto-grants-2011_10
Patent number
US08030500B2

Reaction notes

Loading…