1H-Indazole-5-boronic acid pinacol ester → HCID 88925642, compound

HRID 1478387Notes

Reaction equation

HRID 1478387 reaction equation
Cl[C:2]1[CH:3]=[CH:4][N:5]2[C:10]([C:11]=1[O:12][CH3:13])=[C:9]([CH:14]1[CH2:16][CH2:15]1)[CH:8]=[C:7]([C:17]([O:19][CH3:20])=[O:18])[C:6]2=[O:21].[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[CH:3]=[CH:4][N:5]4[C:10]([C:11]=3[O:12][CH3:13])=[C:9]([CH:14]3[CH2:16][CH2:15]3)[CH:8]=[C:7]([C:17]([O:19][CH3:20])=[O:18])[C:6]4=[O:21])=[CH:28][CH:29]=2)[CH:24]=[N:23]1

Participants

3

Reactant 2

HCID 177504691H-Indazole-5-boronic acid pinacol esterHCID 88925609HCID 88925609, compound

Product 1

HCID 88925642HCID 88925642, compoundYield 51.4%

Procedure

Methyl 8-(1H-indazol-5-yl)-1-cyclopropyl-9-methoxy-4-oxo-4H-quinolizine-3-carboxylate was prepared according to General Procedure A from methyl 8-chloro-1-cyclopropyl-9-methoxy-4-oxo-4H-quinolizine-3-carboxylate (50 mg, 0.16 mmol), and 1H-Indazole-5-boronic acid pinacol ester (47.6 mg, 0.20 mmol). Purification by flash silica column chromatography (DCM:MeOH) (1:0 to 9:1) afforded the title compound as an orange foam (32 mg, 46%).

Workup

  1. customMethyl 8-(1H-indazol-5-yl)-1-cyclopropyl-9-methoxy-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-e90d9fdd624f4ce494b95e1563b3a66b
Source dataset
uspto-grants-2016_08
Patent number
US09403818B2

Reaction notes

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