1H-Indazole-5-boronic acid → 4-amino-5-fluoro-8-(1H-indazol-5-yl)-7-methylcinnoline-3-carboxamide

HRID 2203229Notes

Reaction equation

HRID 2203229 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6](B(O)O)=[CH:7][CH:8]=2)[CH:3]=[N:2]1.[NH2:13][C:14]1[C:23]2[C:18](=[C:19](Br)[C:20]([CH3:25])=[CH:21][C:22]=2[F:24])[N:17]=[N:16][C:15]=1[C:27]([NH2:29])=[O:28]>>[NH2:13][C:14]1[C:23]2[C:18](=[C:19]([C:6]3[CH:5]=[C:4]4[C:9](=[CH:8][CH:7]=3)[NH:1][N:2]=[CH:3]4)[C:20]([CH3:25])=[CH:21][C:22]=2[F:24])[N:17]=[N:16][C:15]=1[C:27]([NH2:29])=[O:28]

Participants

3

Reactant 2

HCID 177505041H-Indazole-5-boronic acidHCID 898254624-Amino-8-bromo-5-fluoro-7-methylcinnoline-3-carboxamide

Product 1

HCID 717656234-amino-5-fluoro-8-(1H-indazol-5-yl)-7-methylcinnoline-3-carboxamide

Procedure

The title compound was prepared in a manner similar to EXAMPLE 1 using (1H-indazol-5-yl)boronic acid and 4-amino-8-bromo-5-fluoro-7-methylcinnoline-3-carboxamide. 1H NMR (400 MHz, CD3OD) δ ppm 2.28 (s, 3 H), 7.19-7.30 (m, 1 H), 7.35 (d, J=16 Hz, 1H), 7.59-7.70 (m, 2 H), 8.07 (s, 1 H); ESI-MS m/z [M+H]+ 337.2.

Sources & evidence

ORD record
ord-fd31805896584bda911209732ebfcc32
Source dataset
uspto-grants-2016_06
Patent number
US09365566B2

Reaction notes

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