2-(Dimethylamino)pyridine-5-boronic acid hydrate → 3-(6-(dimethylamino)pyridin-3-yl)-1H-indazole-6-carbaldehyde

HRID 1615333Notes

Reaction equation

HRID 1615333 reaction equation
[N:1]1[CH:6]=[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.O.[CH3:19][N:20](C)[C:21]1C=CC(B(O)O)=CN=1>>[CH3:19][N:20]([CH3:21])[C:6]1[N:1]=[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]=1

Participants

3

Reactant 2

HCID 441190932-(Dimethylamino)pyridine-5-boronic acid hydrateHCID 866519663-(pyridin-3-yl)-1H-indazole-6-carbaldehyde

Product 1

HCID 866519823-(6-(dimethylamino)pyridin-3-yl)-1H-indazole-6-carbaldehyde

Procedure

According to the procedure for the synthesis of 3-(pyridin-3-yl)-1H-indazole-6-carbaldehyde, except substituting 2-(dimethylamino)pyridine-5-boronic acid hydrate (41 mg, 0.22 mmol), the title compound was prepared as a yellow powder (14 mg, 29%). 1H NMR (400 MHz, d6-DMSO) δ ppm 10.13 (s, 1H), 8.72 (d, J=2.4 Hz, 1H), 8.17-8.16 (m, 2H), 8.09 (dd, J=8.4, 2.1 Hz, 1H), 7.62 (d, J=8.9 Hz, 1H), 6.79 (d, J=8.8 Hz, 1H), 3.09 (s, 6H); MS ESI 267.0 (100) [M+H]+, calcd for [C15H14N4O+H]+ 267.12.

Sources & evidence

ORD record
ord-3fc70031319a42cfae4948bf1677c38b
Source dataset
uspto-grants-2014_07
Patent number
US08765748B2

Reaction notes

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