2-(2-Bromophenoxy)pyrimidine → 5-[3-Fluoro-2'-(pyrimidin-2-yloxy)biphenyl-4-yl]-1H-pyrrolo[2,3-b]pyridine

HRID 1524021Notes

Reaction equation

HRID 1524021 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:39]=[CH:38][CH:37]=[CH:36][C:28]=1[O:29][C:30]1[N:35]=[CH:34][CH:33]=[CH:32][N:31]=1>>[F:1][C:2]1[CH:7]=[C:6]([C:27]2[CH:39]=[CH:38][CH:37]=[CH:36][C:28]=2[O:29][C:30]2[N:31]=[CH:32][CH:33]=[CH:34][N:35]=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 145311902-(2-Bromophenoxy)pyrimidineHCID 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 903132625-[3-Fluoro-2'-(pyrimidin-2-yloxy)biphenyl-4-yl]-1H-pyrrolo[2,3-b]pyridine

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 2-(2-bromophenoxy)pyrimidine. MS (ESI): mass calcd. for C23H15FN4O, 382.12; m/z found, 383.1 [M+H]+. 1H NMR (400 MHz, CDCl3) δ 9.24 (s, 1H), 8.51-8.42 (m, 3H), 8.14-8.05 (m, 1H), 7.57-7.28 (m, 8H), 6.99-6.89 (m, 1H), 6.55 (dd, J=3.6, 1.8, 1H).

Sources & evidence

ORD record
ord-6279444175b6493b9c26291f66e89cd6
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

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