4-Hydroxyphenylboronic acid → HCID 86696753, compound

HRID 1478361Notes

Reaction equation

HRID 1478361 reaction equation
Cl[C:2]1[C:3]([F:22])=[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][CH2:19][CH3:20])=[O:17])[C:6]2=[O:21].[OH:23][C:24]1[CH:29]=[CH:28][C:27](B(O)O)=[CH:26][CH:25]=1>>[OH:23][C:24]1[CH:29]=[CH:28][C:27]([C:2]2[C:3]([F:22])=[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][CH2:19][CH3:20])=[O:17])[C:6]3=[O:21])=[CH:26][CH:25]=1

Participants

3

Reactant 2

HCID 27343604-Hydroxyphenylboronic acidHCID 9927245Ethyl 8-chloro-1-cyclopropyl-7-fluoro-9-methyl-4-oxo-4H-quinolizine-3-carboxylate

Product 1

HCID 86696753HCID 86696753, compoundYield 68%

Procedure

Ethyl 8-(4-hydroxyphenyl)-1-cyclopropyl-7-fluoro-9-methyl-4-oxo-4H-quinolizine-3-carboxylate was prepared according to General Procedure A from ethyl 8-chloro-1-cyclopropyl-7-fluoro-9-methyl-4-oxo-4H-quinolizine-3-carboxylate (100 mg, 0.34 mmol) and (4-hydroxyphenyl)boronic acid (55.4 mg, 0.40 mmol). Purification by flash silica column chromatography (DCM:MeOH) (1:0 to 9:1) afforded the title compound as a yellow solid (80 mg, 68%).

Workup

  1. customEthyl 8-(4-hydroxyphenyl)-1-cyclopropyl-7-fluoro-9-methyl-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-cf0ceb1f84094ed195ef3a14d84a8d19
Source dataset
uspto-grants-2016_08
Patent number
US09403818B2

Reaction notes

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