(R)-2-bromo-N-(1-hydroxypropan-2-yl)benzenesulfonamide → 3'-Fluoro-N-[(1R)-2-hydroxy-1-methylethyl]-4'-(1H-pyrrolo[2,3-b]pyridin-5-yl)biphenyl-2-sulfonamide

HRID 1523905Notes

Reaction equation

HRID 1523905 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[CH:18]=[C:19]2[CH:25]=[CH:24][NH:23][C:20]2=[N:21][CH:22]=1.Br[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[S:33]([NH:36][C@H:37]([CH3:40])[CH2:38][OH:39])(=[O:35])=[O:34]>>[F:1][C:2]1[CH:7]=[C:6]([C:27]2[C:28]([S:33]([NH:36][C@H:37]([CH3:40])[CH2:38][OH:39])(=[O:35])=[O:34])=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:5]=[CH:4][C:3]=1[C:17]1[CH:18]=[C:19]2[CH:25]=[CH:24][NH:23][C:20]2=[N:21][CH:22]=1

Participants

3

Reactant 2

HCID 79027397(R)-2-bromo-N-(1-hydroxypropan-2-yl)benzenesulfonamideHCID 903129005-(2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 903137123'-Fluoro-N-[(1R)-2-hydroxy-1-methylethyl]-4'-(1H-pyrrolo[2,3-b]pyridin-5-yl)biphenyl-2-sulfonamide

Procedure

The title compound was prepared using methods analogous to those described in Example 376 using 5-(2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1H-pyrrolo[2,3-b]pyridine and (R)-2-bromo-N-(1-hydroxypropan-2-yl)benzenesulfonamide. MS (ESI): mass calcd. for C22H20FN3O3S, 425.12; m/z found, 426.0 [M+H]+. 1H NMR (400 MHz, CDCl3) δ 9.65 (s, 1H), 8.30-8.19 (m, 2H), 7.93-7.84 (m, 1H), 7.69-7.61 (m, 1H), 7.61-7.53 (m, 1H), 7.44-7.31 (m, 4H), 7.27 (d, J=7.8, 1H), 6.56-7.47 (m, 1H), 6.07 (d, J=6.5, 1H), 3.57 (t, J=7.0, 1H), 3.49-3.32 (m, 2H), 2.41 (s, 1H), 1.04 (d, J=6.4, 3H).

Sources & evidence

ORD record
ord-0c1d6d3345e64b6f8b0f7ffa877092fb
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

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