1H-Pyrazole-5-boronic acid → 3-(1H-pyrazol-5-yl)-1H-indazole-6-carbaldehyde

HRID 1615307Notes

Reaction equation

HRID 1615307 reaction equation
N1C=[CH:5][CH:4]=[C:3]([C:7]2[C:15]3[C:10](=[CH:11][C:12]([CH:16]=[O:17])=[CH:13][CH:14]=3)[NH:9][N:8]=2)C=1.[NH:18]1C(B(O)O)=CC=[N:19]1>>[NH:18]1[C:3]([C:7]2[C:15]3[C:10](=[CH:11][C:12]([CH:16]=[O:17])=[CH:13][CH:14]=3)[NH:9][N:8]=2)=[CH:4][CH:5]=[N:19]1

Participants

3

Reactant 2

HCID 112519791H-Pyrazole-5-boronic acidHCID 866519663-(pyridin-3-yl)-1H-indazole-6-carbaldehyde

Product 1

HCID 866519693-(1H-pyrazol-5-yl)-1H-indazole-6-carbaldehyde

Procedure

According to the procedure for the synthesis of 3-(pyridin-3-yl)-1H-indazole-6-carbaldehyde, except substituting 1H-pyrazole-5-boronic acid (25 mg, 0.22 mmol), the title compound was prepared as a beige solid (5.3 mg, 13%). 1H NMR (400 MHz, CD3OD) δ ppm 10.13 (s, 1H), 8.44-8.32 (br. m, 1H), 8.14 (s, 1H), 7.78 (d, J=1.8 Hz, 1H), 7.75 (d, J=8.3 Hz, 1H), 6.90 (d, J=2.0 Hz, 1H); MS ESI 213.0 (100) [M+H]+, calcd for [C11H8N4O+H]+ 213.07.

Sources & evidence

ORD record
ord-e9c71f7c8b4f458d815bba15914289b8
Source dataset
uspto-grants-2014_07
Patent number
US08765748B2

Reaction notes

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