(Pyridin-4-yl)boronic acid → HCID 18406911, compound

HRID 1016407Notes

Reaction equation

HRID 1016407 reaction equation
[N:1]1[CH:6]=[CH:5][C:4](B(O)O)=[CH:3][CH:2]=1.Br[C:11]1[C:12]([O:27][CH2:28][C:29]2[N:30]([CH2:34][CH3:35])[N:31]=[CH:32][N:33]=2)=[N:13][N:14]2[C:19]=1[CH:18]=[N:17][N:16]=[C:15]2[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[F:26]>>[CH2:34]([N:30]1[C:29]([CH2:28][O:27][C:12]2[C:11]([C:4]3[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=3)=[C:19]3[N:14]([C:15]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=4[F:26])=[N:16][N:17]=[CH:18]3)[N:13]=2)=[N:33][CH:32]=[N:31]1)[CH3:35]

Participants

3

Reactant 2

HCID 2734379(Pyridin-4-yl)boronic acidHCID 18406952HCID 18406952, compound

Product 1

HCID 18406911HCID 18406911, compoundYield 21%

Procedure

This was prepared in 21% yield using a similar procedure to that described in Example 18 except using pyridine-4-boronic acid instead of 3-trifluoromethylbenzeneboronic acid and 3-bromo-2-(2-ethyl-2H-[1,2,4]triazol-3-ylmethoxy)-7-(2-fluorophenyl)pyrazolo[1,5-d][1,2,4]triazine instead of 3-bromo-7-(2-fluorophenyl)-2-(2-methyl-2H-[1,2,4]triazol-3-ylmethoxy)pyrazolo[1,5-d][1,2,4]triazine. Data for title compound: mp=214-217° C.; 1H NMR (360 MHz, CDCl3) δ 1.35 (3H, t, J=7.2 Hz), 4.12 (2H, q, J=7.2 Hz), 5.60 (2H, s), 7.31 (1H, t, J=9.2 Hz), 7.42 (1H, t, J=7.6 Hz), 7.62 (2H, d, J=6.0 Hz), 7.68 (1H, m), 7.82 (1H, m), 7.90 (1H, s), 8.72 (2H, d, J=5.6 Hz), 9.53 (1H, s); MS (ES+) m/e 417 [MH]+.

Workup

  1. customThis was prepared in 21% yield

Sources & evidence

ORD record
ord-51929fbeaf9642eea067712e24c51bd6
Source dataset
uspto-grants-2002_11
Patent number
US06476030B1

Reaction notes

Loading…