5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine → HCID 88925667, compound

HRID 1478384Notes

Reaction equation

HRID 1478384 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].[NH2:22][C:23]1[CH:28]=[CH:27][C:26](B2OC(C)(C)C(C)(C)O2)=[CH:25][N:24]=1>>[NH2:22][C:23]1[N:24]=[CH:25][C:26]([C:2]2[C:3]([CH3:21])=[CH:4][N:5]3[C:10]([C:11]=2[CH3:12])=[C:9]([CH:13]2[CH2:15][CH2:14]2)[CH:8]=[C:7]([C:16]([O:18][CH3:19])=[O:17])[C:6]3=[O:20])=[CH:27][CH:28]=1

Participants

3

Reactant 2

HCID 27565555-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amineHCID 88925635HCID 88925635, compound

Product 1

HCID 88925667HCID 88925667, compoundYield 75.7%

Procedure

Methyl 8-(6-amino-pyridin-3-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, 0.16 mmol) and 2-amino-pyridine-5-boronic acid pinacol ester (43 mg, 0.20 mmol). Purification by flash silica column chromatography (DCM:MeOH) (1:0 to 25:4) afforded the title compound as a yellow solid (44 mg, 69%).

Workup

  1. customMethyl 8-(6-amino-pyridin-3-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 25:4)

Sources & evidence

ORD record
ord-f0325c5c567c4ca08841207b90c4e6e1
Source dataset
uspto-grants-2016_08
Patent number
US09403818B2

Reaction notes

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