ethyl 4-bromo-5-methyl-1H-pyrazole-3-carboxylate → 4-bromo-N,N-dibutyl-5-methyl-1H-pyrazole-3-carboxamide

HRID 528920Notes

Reaction equation

HRID 528920 reaction equation
[CH2:1]([N:5]([CH2:15][CH2:16][CH2:17][CH3:18])[C:6]([C:8]1[C:12](Cl)=[C:11]([CH3:14])[NH:10][N:9]=1)=[O:7])[CH2:2][CH2:3][CH3:4].[Br:19]C1C(C(OCC)=O)=NNC=1C>>[Br:19][C:12]1[C:8]([C:6]([N:5]([CH2:15][CH2:16][CH2:17][CH3:18])[CH2:1][CH2:2][CH2:3][CH3:4])=[O:7])=[N:9][NH:10][C:11]=1[CH3:14]

Participants

3

Reactant 2

HCID 616098ethyl 4-bromo-5-methyl-1H-pyrazole-3-carboxylateHCID 71062189N,N-dibutyl-4-chloro-5-methyl-1H-pyrazole-3-carboxamide

Product 1

HCID 473701634-bromo-N,N-dibutyl-5-methyl-1H-pyrazole-3-carboxamideYield 75%

Procedure

Following a procedure analogous to that for the synthesis of Intermediate 1B, ethyl 4-bromo-5-methyl-1H-pyrazole-3-carboxylate (Tabrizi, M. A. et al., Bioorg. Med. Chem., 16:2419-2430 (2008)) (5.68 g, 24.4 mmol) was converted to the title compound (5.79 g, 75%). 1H NMR (CDCl3) δ 3.51 (t, J=7.4 Hz, 2H), 3.38-3.26 (m, 2H), 2.34 (s, 3H), 1.73-1.34 (m, 6H), 1.22-1.13 (m, 2H), 1.03-0.75 (m, 6H); MS(ESI+) m/z 316.2 (M+H)+.

Sources & evidence

ORD record
ord-f623520f9c7149d39e8e4bea76b97e97
Source dataset
uspto-grants-2016_05
Patent number
US09346795B2

Reaction notes

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