Methyl 3-amino-2-bromobenzoate → HCID 89655469, compound

HRID 1775199Notes

Reaction equation

HRID 1775199 reaction equation
[NH2:1][C:2]1[C:3]([Br:12])=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[O:13]=[C:14]1[CH2:19][C:18](=O)[CH2:17][N:16]([C:21]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:22])[CH2:15]1>C(O)(=O)C>[Br:12][C:3]1[C:4]([C:5]([O:7][CH3:8])=[O:6])=[CH:9][CH:10]=[CH:11][C:2]=1[NH:1][C:18]1[CH2:17][N:16]([C:21]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:22])[CH2:15][C:14](=[O:13])[CH:19]=1

Participants

4

Reactant 2

HCID 13574117Methyl 3-amino-2-bromobenzoateHCID 49761164Phenylmethyl 3,5-dioxo-1-piperidinecarboxylate

Product 1

HCID 89655469HCID 89655469, compoundYield 51.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
70 °C

Procedure

Methyl 3-amino-2-bromobenzoate (0.25 g, 1.1 mmol) and benzyl 3,5-dioxopiperidine-1-carboxylate (0.13 g, 0.55 mmol) were dissolved in 10 mL of acetic acid at 25° C., under nitrogen. The mixture was stirred for 8 hours at 70° C. The resultant solid was purified by chromatography column on silica gel (elution with hexane/ethyl acetate) to afford 0.13 g (51%) of benzyl 3-((2-bromo-3-(methoxycarbonyl)phenyl)amino)-5-oxo-5,6-dihydropyridine-1(2H)-carboxylate as a tan foam. 1H NMR (CDCl3-d1) δ 7.53-7.58 (m, 3H), 7.42-7.48 (m, 5H), 5.56 (s, 1H), 5.16 (s, 2H), 4.46 (s, 2H), 4.13 (s, 2H), 3.93 (s, 3H). MS (ESI) m/e [M+1]+ 459.0.

Workup

  1. customThe resultant solid was purified by chromatography column on silica gel (elution with hexane/ethyl acetate)

Sources & evidence

ORD record
ord-c5229102e88a48fea8c753bb7150b654
Source dataset
uspto-grants-2016_02
Patent number
US09260440B2

Reaction notes

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