(Pyridin-4-yl)boronic acid → 3-(pyridin-4-yl)-1H-indazole-6-carbaldehyde
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)[CH:2]=1.[N:18]1C=CC(B(O)O)=C[CH:19]=1>>[N:18]1[CH:19]=[CH:2][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]=1Participants
3
Procedure
According to the procedure for the synthesis of 3-(pyridin-3-yl)-1H-indazole-6-carbaldehyde, except substituting pyridin-4-ylboronic acid (27 mg, 0.22 mmol), the title compound was obtained as a beige solid (3.7 mg, 9%). 1H NMR (400 MHz, CD3OD) δ ppm 10.15 (s, 1H), 8.69 (d, J=6.3 Hz, 2H), 8.32 (d, J=8.8 Hz, 1H), 8.22 (s, 1H), 8.10 (d, J=6.3 Hz, 2H), 7.84 (d, J=6.3 Hz, 1H); MS ESI 224.0 (100) [M+H]+, calcd for [C13H9N3O+H]+ 224.07.
Sources & evidence
- ORD record
- ord-ee742b44e5744837971c168b71d71945
- Source dataset
- uspto-grants-2014_07