1H-Indazole-5-boronic acid pinacol ester → HCID 88925654, compound

HRID 1478385Notes

Reaction equation

HRID 1478385 reaction equation
Cl[C:2]1[C:3]([CH3:21])=[CH:4][N:5]2[C:10]([C:11]=1[CH3:12])=[C:9]([CH:13]1[CH2:15][CH2:14]1)[CH:8]=[C:7]([C:16]([O:18][CH3:19])=[O:17])[C:6]2=[O:20].[NH:22]1[C:30]2[C:25](=[CH:26][C:27](B3OC(C)(C)C(C)(C)O3)=[CH:28][CH:29]=2)[CH:24]=[N:23]1>>[NH:22]1[C:30]2[C:25](=[CH:26][C:27]([C:2]3[C:3]([CH3:21])=[CH:4][N:5]4[C:10]([C:11]=3[CH3:12])=[C:9]([CH:13]3[CH2:15][CH2:14]3)[CH:8]=[C:7]([C:16]([O:18][CH3:19])=[O:17])[C:6]4=[O:20])=[CH:28][CH:29]=2)[CH:24]=[N:23]1

Participants

3

Reactant 2

HCID 177504691H-Indazole-5-boronic acid pinacol esterHCID 88925635HCID 88925635, compound

Product 1

HCID 88925654HCID 88925654, compoundYield 45.5%

Procedure

Methyl 8-(1H-indazol-5-yl)-1-cyclopropyl-7,9-dimethyl-4-oxo-4H-quinolizine-3-carboxylate was prepared according to General Procedure A from methyl 8-chloro-1-cyclopropyl-7,9-dimethyl-4-oxo-4H-quinolizine-3-carboxylate (50 mg, 0.17 mmol), and 1H-Indazole-5-boronic acid pinacol ester (48 mg, 0.19 mmol). Purification by flash silica column chromatography (DCM:MeOH) (1:0 to 9:1) afforded the title compound as a yellow solid (30 mg, 45%).

Workup

  1. customMethyl 8-(1H-indazol-5-yl)-1-cyclopropyl-7,9-dimethyl-4-oxo-4H-quinolizine-3-carboxylate was prepared
  2. customPurification by flash silica column chromatography (DCM:MeOH) (1:0 to 9:1)

Sources & evidence

ORD record
ord-658ce6a7fae34e88b841ec673bcdfd82
Source dataset
uspto-grants-2016_08
Patent number
US09403818B2

Reaction notes

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