2-Fluoropyridine-4-boronic acid → HCID 86696562, compound

HRID 1854844Notes

Reaction equation

HRID 1854844 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:27]=[C:26](B(O)O)[CH:25]=[CH:24][N: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:26]2[CH:25]=[CH:24][N:23]=[C:22]([F:21])[CH:27]=2)[CH:3]=[CH:4]3)[CH2:15][CH2:14]1

Participants

3

Reactant 2

HCID 27833962-Fluoropyridine-4-boronic acidHCID 86696543Methyl 8-chloro-1-cyclopropyl-9-methyl-4-oxo-quinolizine-3-carboxylate

Product 1

HCID 86696562HCID 86696562, compoundYield 89.3%

Procedure

Methyl 1-cyclopropyl-8-(2-fluoro-pyridin-4-yl)-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 (100 mg, 0.34 mmol) and 2-fluoro-pyridin-4-yl-boronic acid (72 mg, 0.51 mmol). Purification by flash silica column chromatography (CH2Cl2:MeOH) (1:0 to 94:6) afforded the title compound as a yellow solid (107 mg, 89%). ESI-MS m/z: 353 (M+H)+.

Workup

  1. customMethyl 1-cyclopropyl-8-(2-fluoro-pyridin-4-yl)-9-methyl-4-oxo-4H-quinolizine-3-carboxylate was prepared
  2. customPurification by flash silica column chromatography (CH2Cl2:MeOH) (1:0 to 94:6)

Sources & evidence

ORD record
ord-1c9b4fec2cd34e10b567cf54569d2070
Source dataset
uspto-grants-2015_02
Patent number
US08962842B2

Reaction notes

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