Iodoethane → methyl 5-chloro-3-(ethyl(tetrahydro-2H-pyran-4-yl)amino)-2-methylbenzoate

HRID 2208768Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([NH:13][CH:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[C:5]([CH3:12])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:26](I)[CH3:27]>O=[N+]([O-])[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[Ce+4].[NH4+].[NH4+]>[Cl:1][C:2]1[CH:3]=[C:4]([N:13]([CH2:26][CH3:27])[CH:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[C:5]([CH3:12])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8]

Participants

Conditions

Temperature: 80 °C

Procedure

To a stirred solution of methyl 5-chloro-2-methyl-3-((tetrahydro-2H-pyran-4-yl)amino)benzoate (0.5 g, 1.76 mmol) in dry CAN (15 mL), cesium carbonate (1.2 g, 3.68 mmol) and ethyl iodide (2.7 g, 17.3 mmol) were added and the resulting reaction mixture was heated at 80° C. for 18 h. On completion, the mixture was cooled to room temperature and filtered with the residue washed with ethyl acetate. The filtrate was concentrated and then purified by column chromatography to afford desired methyl 5-chloro-3-(ethyl(tetrahydro-2H-pyran-4-yl)amino)-2-methylbenzoate (0.180 g, 34%).

Workup

customthe resulting reaction mixture
temperatureOn completion, the mixture was cooled to room temperature
filtrationfiltered with the residue
washwashed with ethyl acetate
concentrationThe filtrate was concentrated
custompurified by column chromatography

Sources & evidence

ORD record: ord-82032b20fd2445e09b762c5a123dae1b
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09376422B2

Reaction notes

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