5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine → HCID 88925611, compound

HRID 1478386Notes

Reaction equation

HRID 1478386 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].[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[CH:3]=[CH:4][N:5]3[C:10]([C:11]=2[O:12][CH3:13])=[C:9]([CH:14]2[CH2:16][CH2:15]2)[CH:8]=[C:7]([C:17]([O:19][CH3:20])=[O:18])[C:6]3=[O:21])=[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 88925609HCID 88925609, compound

Product 1

HCID 88925611HCID 88925611, compoundYield 59.9%

Procedure

Methyl 8-(6-amino-pyridin-3-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 2-aminopyridine-5-boronic acid pinacol ester (42.9 mg, 0.20 mmol). Purification by flash silica column chromatography (DCM:MeOH) (1:0 to 9:1) afforded the title compound as an orange solid (35 mg, 57%).

Workup

  1. customMethyl 8-(6-amino-pyridin-3-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-acc7835b845a4303af3b4e4c42bb4e2e
Source dataset
uspto-grants-2016_08
Patent number
US09403818B2

Reaction notes

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