5-(2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1H-pyrrolo[2,3-b]pyridine → 2-{[3'-Fluoro-4'-(1H-pyrrolo[2,3-b]pyridin-5-yl)biphenyl-2-yl]oxy}pyrimidin-4-amine

HRID 1524020Notes

Reaction equation

HRID 1524020 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:40]=[CH:39][CH:38]=[CH:37][C:28]=1[O:29][C:30]1[N:35]=[C:34]([NH2:36])[CH:33]=[CH:32][N:31]=1>>[F:1][C:2]1[CH:7]=[C:6]([C:27]2[CH:40]=[CH:39][CH:38]=[CH:37][C:28]=2[O:29][C:30]2[N:35]=[C:34]([NH2:36])[CH:33]=[CH:32][N:31]=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 903130522-(2-Bromophenoxy)pyrimidin-4-amine

Product 1

HCID 903138462-{[3'-Fluoro-4'-(1H-pyrrolo[2,3-b]pyridin-5-yl)biphenyl-2-yl]oxy}pyrimidin-4-amine

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)pyrimidin-4-amine. MS (ESI): mass calcd. for C23H16FN5O, 397.13; m/z found, 398.1 [M+H]+. 1H NMR (400 MHz, CDCl3) δ 8.94 (s, 1H), 8.47 (s, 1H), 8.11 (d, J=2.1, 1H), 7.96 (d, J=5.7, 1H), 7.54-7.30 (m, 9H), 6.07 (d, J=5.7, 1H), 4.96-4.85 (m, 2H).

Sources & evidence

ORD record
ord-ffee1e602f4c43ed8afe89610e559894
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

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