4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole → HCID 67467128, compound

HRID 85499Notes

Reaction equation

HRID 85499 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:15]([O:17][CH3:18])=[O:16])[C:5]2[C:6]([CH3:14])=[N:7][N:8]([CH:11]([CH3:13])[CH3:12])[C:9]=2[CH:10]=1.CC1(C)C(C)(C)OB([C:27]2[CH:28]=[N:29][NH:30][CH:31]=2)O1>>[CH:11]([N:8]1[C:9]2[CH:10]=[C:2]([C:27]3[CH:28]=[N:29][NH:30][CH:31]=3)[CH:3]=[C:4]([C:15]([O:17][CH3:18])=[O:16])[C:5]=2[C:6]([CH3:14])=[N:7]1)([CH3:13])[CH3:12]

Participants

3

Reactant 2

HCID 27740104-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 67466747Methyl 6-bromo-1-isopropyl-3-methyl-1H-indazole-4-carboxylate

Product 1

HCID 67467128HCID 67467128, compound

Conditions

Temperature
115 °C

Procedure

The title compound was prepared in the same manner as described for example 80 (step a) from methyl 6-bromo-1-isopropyl-3-methyl-1H-indazole-4-carboxylate (0.5 g, 1.60 mmol) and 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (0.37 g, 1.92 mmol) wherein the reaction mixture was heated at 115° C. for 3 h. The crude compound was purified silica gel chromatography (eluent: 50% ethyl acetate\pet ether) to afford the title compound as an off-white solid. 1H NMR (DMSO-d6, 400 MHz): 1.470 (d, J=6.4 Hz, 6H), 2.543 (s, 3H), 3.928 (s, 3H), 5.000-5.063 (m, 1H), 7.822 (s, 1H), 8.102 (d, J=9.6 Hz, 2H), 8.374 (s, 1H), 13.030 (brs, 1H). LCMS (ES+) m/z: 299.25.

Workup

  1. customThe title compound was prepared in the same manner
  2. customThe crude compound was purified silica gel chromatography (eluent: 50% ethyl acetate\pet ether)

Sources & evidence

ORD record
ord-c58c40fde6e74b9ca5c65095358b5cb2
Source dataset
uspto-grants-2014_09
Patent number
US08846935B2

Reaction notes

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