Thiophene-3-boronic acid → HCID 18406844, compound

HRID 1016426Notes

Reaction equation

HRID 1016426 reaction equation
[S:1]1[CH:5]=[CH:4][C:3](B(O)O)=[CH:2]1.Br[C:10]1[C:11]([O:26][CH2:27][C:28]2[N:29]([CH2:33][CH3:34])[N:30]=[CH:31][N:32]=2)=[N:12][N:13]2[C:18]=1[CH:17]=[N:16][N:15]=[C:14]2[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[F:25]>>[CH2:33]([N:29]1[C:28]([CH2:27][O:26][C:11]2[C:10]([C:3]3[CH:4]=[CH:5][S:1][CH:2]=3)=[C:18]3[N:13]([C:14]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=4[F:25])=[N:15][N:16]=[CH:17]3)[N:12]=2)=[N:32][CH:31]=[N:30]1)[CH3:34]

Participants

3

Reactant 2

HCID 581760Thiophene-3-boronic acidHCID 18406952HCID 18406952, compound

Product 1

HCID 18406844HCID 18406844, compoundYield 86%

Procedure

This was prepared in 86% yield using a similar procedure to that described in Example 18 except using thiophene-3-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=187-193° C. (CH2Cl2-EtOAc); 1H NMR (400 MHz, CDCl3) δ 1.35 (3H, t, J=7.3 Hz), 4.14 (2H, q, J=7.3 Hz), 5.59 (2H, s), 7.29 (1H, m), 7.40 (1H, td, J=7.6 and 0.8 Hz), 7.48 (1H, s), 7.49 (1H, s), 7.64-7.66 (2H, m), 7.81 (1H, m), 7.90 (1H, s), 9.46 (1H, s); MS (ES+) m/e 422 [MH]+; Anal. Found C, 56.14; H, 3.84; N, 22.75%. C20H16FN7OS.0.3H2O requires C, 56.28; H, 3.92; N, 22.97%.

Workup

  1. customThis was prepared in 86% yield

Sources & evidence

ORD record
ord-0c1e6a8ae6ea451fa68919dea654e268
Source dataset
uspto-grants-2002_11
Patent number
US06476030B1

Reaction notes

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