5-(2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1H-pyrrolo[2,3-b]pyridine → HCID 90313389, compound

HRID 1524159Notes

Reaction equation

HRID 1524159 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[C:28]([S:33]([CH:36]([CH3:38])[CH3:37])(=[O:35])=[O:34])=[N:29][CH:30]=[CH:31][CH:32]=1>>[F:1][C:2]1[CH:7]=[C:6]([C:27]2[C:28]([S:33]([CH:36]([CH3:38])[CH3:37])(=[O:34])=[O:35])=[N: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 903129005-(2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1H-pyrrolo[2,3-b]pyridineHCID 90313763HCID 90313763, compound

Product 1

HCID 90313389HCID 90313389, compound

Procedure

The title compound was prepared as described in step D of Example 803 using 5-(2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1H-pyrrolo[2,3-b]pyridine and 3-bromo-2-(isopropylsulfonyl)pyridine. MS (ESI): mass calcd. for C21H18FN4O2S, 395.11; m/z found, 396.1 [M+H]+. 1H NMR (400 MHz, CDCl3) δ 9.45 (s, 1H), 8.70 (dd, J=4.6, 1.6, 2H), 8.25-8.17 (m, 1H), 7.84 (dd, J=7.8, 1.7, 1H), 7.64-7.54 (m, 2H), 7.46-7.32 (m, 3H), 6.61 (s, 1H), 4.26 (hept, J=6.8, 1H), 1.34 (d, J=6.9, 6H).

Sources & evidence

ORD record
ord-59888f7792654d96b9bfb0bfd700e5bc
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

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