4-Hydroxyphenylboronic acid → HCID 86696580, compound

HRID 1854868Notes

Reaction equation

HRID 1854868 reaction equation
Cl[C:2]1[CH:3]=[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].[OH:21][C:22]1[CH:27]=[CH:26][C:25](B(O)O)=[CH:24][CH:23]=1>>[CH:13]1([C:9]2[CH:8]=[C:7]([C:16]([O:18][CH3:19])=[O:17])[C:6](=[O:20])[N:5]3[C:10]=2[C:11]([CH3:12])=[C:2]([C:25]2[CH:26]=[CH:27][C:22]([OH:21])=[CH:23][CH:24]=2)[CH:3]=[CH:4]3)[CH2:15][CH2:14]1

Participants

3

Reactant 2

HCID 27343604-Hydroxyphenylboronic acidHCID 86696543Methyl 8-chloro-1-cyclopropyl-9-methyl-4-oxo-quinolizine-3-carboxylate

Product 1

HCID 86696580HCID 86696580, compoundYield 102.1%

Procedure

Methyl 1-cyclopropyl-8-(4-hydroxy-phenyl)-9-methyl-4-oxo-4H-quinolizine-3-carboxylate was prepared according to General Procedure A using methyl 8-chloro-1-cyclopropyl-9-methyl-4-oxo-4H-quinolizine-3-carboxylate (500 mg, 1.71 mmol) and 4-hydroxy-phenyl-boronic acid (283 mg, 2.06 mmol). Purification by flash silica column chromatography (CH2Cl2:MeOH) (1:0 to 9:1) afforded the title compound as a yellow solid (610 mg, 100%). ESI-MS m/z: 388 (M+K)+, 372 (M+Na)+, 350 (M+H)+.

Workup

  1. customMethyl 1-cyclopropyl-8-(4-hydroxy-phenyl)-9-methyl-4-oxo-4H-quinolizine-3-carboxylate was prepared
  2. customPurification by flash silica column chromatography (CH2Cl2:MeOH) (1:0 to 9:1)

Sources & evidence

ORD record
ord-6b33fa77a1004641a0649795e445ff65
Source dataset
uspto-grants-2015_02
Patent number
US08962842B2

Reaction notes

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