3-Fluoropyridine-4-boronic acid → HCID 86696749, compound

HRID 1478358Notes

Reaction equation

HRID 1478358 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]=[N:24][CH:25]=[CH:26][C:27]=1B(O)O>>[F:21][C:22]1[CH:23]=[N:24][CH:25]=[CH:26][C:27]=1[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]

Participants

3

Reactant 2

HCID 27793533-Fluoropyridine-4-boronic acidHCID 86696543Methyl 8-chloro-1-cyclopropyl-9-methyl-4-oxo-quinolizine-3-carboxylate

Product 1

HCID 86696749HCID 86696749, compoundYield 65.1%

Procedure

Methyl 8-(3-fluoropyridin-4-yl)-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-fluoropyridin-4-yl)-boronic acid (65.3 mg, 0.41 mmol). Purification by flash silica column chromatography (DCM:MeOH) (1:0 to 9:1) afforded the title compound as a yellow solid (78 mg, 65%).

Workup

  1. customMethyl 8-(3-fluoropyridin-4-yl)-1-cyclopropyl-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-844d51876eae4d2b96522b67dcec8c65
Source dataset
uspto-grants-2016_08
Patent number
US09403818B2

Reaction notes

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