3-Aminophenylboronic acid → HCID 86696547, compound

HRID 1854829Notes

Reaction equation

HRID 1854829 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].[NH2:23][C:24]1[CH:25]=[C:26](B(O)O)[CH:27]=[CH:28][CH:29]=1>>[NH2:23][C:24]1[CH:29]=[C:28]([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:27]=[CH:26][CH:25]=1

Participants

3

Reactant 2

HCID 922693-Aminophenylboronic acidHCID 9927245Ethyl 8-chloro-1-cyclopropyl-7-fluoro-9-methyl-4-oxo-4H-quinolizine-3-carboxylate

Product 1

HCID 86696547HCID 86696547, compoundYield 25%

Procedure

Ethyl 8-(3-amino-phenyl)-1-cyclopropyl-7-fluoro-9-methyl-4-oxo-4H-quinolizine-3-carboxylate was prepared according to General Procedure A using ethyl 8-chloro-1-cyclopropyl-7-fluoro-9-methyl-4-oxo-4H-quinolizine-3-carboxylate (102.5 mg, 0.32 mmol) and (3-amino-phenyl)-boronic acid (54.8 mg, 0.40 mmol). Purification by flash silica column chromatography (CH2Cl2:MeOH) (1:0 to 9:1) afforded the title compound as a yellow solid (30 mg, 25%). ESI-MS m/z: 381 (M+H)+.

Workup

  1. customEthyl 8-(3-amino-phenyl)-1-cyclopropyl-7-fluoro-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-6b6c1dd0875346bcbcef2f2f5c66134b
Source dataset
uspto-grants-2015_02
Patent number
US08962842B2

Reaction notes

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