(5-bromo-1-methyl-1H-pyrazol-4-yl)methanol → 5-bromo-1-methyl-1H-pyrazole-4-carbaldehyde

Reaction equation

[Br:1][C:2]1[N:6]([CH3:7])[N:5]=[CH:4][C:3]=1[CH2:8][OH:9].C(C1C=CC(N2C(C=O)=CN=C2)=CC=1)C>>[Br:1][C:2]1[N:6]([CH3:7])[N:5]=[CH:4][C:3]=1[CH:8]=[O:9]

Participants

Reactant 2

HCID 84662962(5-bromo-1-methyl-1H-pyrazol-4-yl)methanol

HCID 867125651-(4-ethylphenyl)-1H-imidazole-5-carbaldehyde

Product 1

HCID 547753935-bromo-1-methyl-1H-pyrazole-4-carbaldehyde

Procedure

(5-Bromo-1-methyl-1H-pyrazol-4-yl)methanol (C23) was converted to the product using a procedure analogous to that described for the synthesis of 1-(4-ethylphenyl)-1H-imidazole-5-carbaldehyde (C19) in Example 5, step 3. In this case, no chromatography was carried out. Yield: 1.46 g, 7.72 mmol, 92%. LCMS m/z 191.2 (M+1). 1H NMR (400 MHz, CDCl3) δ 3.93 (s, 3H), 7.96 (s, 1H), 9.76 (s, 1H).

Sources & evidence

ORD record: ord-63035b714f6c4ae0a51dcc15846a9d04
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08829010B2

Reaction notes

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