(3-Fluoro-4-hydroxyphenyl)boronic acid → HCID 86696762, compound

HRID 1478369Notes

Reaction equation

HRID 1478369 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].[F:21][C:22]1[CH:23]=[C:24](B(O)O)[CH:25]=[CH:26][C:27]=1[OH:28]>>[F:21][C:22]1[CH:23]=[C:24]([C:2]2[CH:3]=[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:25]=[CH:26][C:27]=1[OH:28]

Participants

3

Reactant 2

HCID 23005361(3-Fluoro-4-hydroxyphenyl)boronic acidHCID 86696543Methyl 8-chloro-1-cyclopropyl-9-methyl-4-oxo-quinolizine-3-carboxylate

Product 1

HCID 86696762HCID 86696762, compoundYield 76.1%

Procedure

Methyl 8-(3-fluoro-4-hydroxyphenyl)-1-cyclopropyl-9-methyl-4-oxo-4H-quinolizine-3-carboxylate was prepared according to General Procedure A from methyl 8-chloro-1-cyclopropyl-9-methyl-4-oxo-4H-quinolizine-3-carboxylate (100 mg, 0.34 mmol) and (3-fluoro-4-hydroxyphenyl)boronic acid (64.1 mg, 0.41 mmol). The residue was rinsed with DCM and dried in a vacuum stove to afford the title compound as a yellow solid (95 mg, 76%).

Workup

  1. customMethyl 8-(3-fluoro-4-hydroxyphenyl)-1-cyclopropyl-9-methyl-4-oxo-4H-quinolizine-3-carboxylate was prepared
  2. washThe residue was rinsed with DCM
  3. customdried in a vacuum stove

Sources & evidence

ORD record
ord-b04f7c52f4e646caae738efabcae5ff9
Source dataset
uspto-grants-2016_08
Patent number
US09403818B2

Reaction notes

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