Cesium carbonate → 3-{4-[2-Methyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-ylmethoxy]-5,6,7,8-tetrahydro-naphthalen-1-yl}-propionic Acid Ethyl Ester

HRID 1726989Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:18])[CH2:5][CH2:6][C:7]1[C:16]2[CH2:15][CH2:14][CH2:13][CH2:12][C:11]=2[C:10]([OH:17])=[CH:9][CH:8]=1)[CH3:2].Cl[CH2:20][C:21]1[C:22]([CH3:37])=[N:23][C:24]([C:27]2[CH:32]=[CH:31][C:30]([C:33]([F:36])([F:35])[F:34])=[CH:29][CH:28]=2)=[CH:25][CH:26]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C>[CH2:1]([O:3][C:4](=[O:18])[CH2:5][CH2:6][C:7]1[C:16]2[CH2:15][CH2:14][CH2:13][CH2:12][C:11]=2[C:10]([O:17][CH2:20][C:21]2[C:22]([CH3:37])=[N:23][C:24]([C:27]3[CH:28]=[CH:29][C:30]([C:33]([F:36])([F:34])[F:35])=[CH:31][CH:32]=3)=[CH:25][CH:26]=2)=[CH:9][CH:8]=1)[CH3:2]

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 103 mg (0.41 mmol) of the above prepared 3-(4-hydroxy-5,6,7,8-tetrahydro-naphthalen-1-yl)-propionic acid ethyl ester, 118 mg (0.41 mmol) of 3-chloromethyl-2-methyl-6-(4-trifluoromethyl-phenyl)-pyridine (example 4G]) and 175 mg (0.54 mmol) of cesium carbonate in 5 ml of acetonitrile was stirred at 60° C. for 2 hours. Then, the solvent was evaporated i. V. and the residue was chromatographed on SiO2 with a mixture of dichloromethane and tert.-butyl methyl ether (98:2, vol./vol.) as eluent. Thereby, 169 mg of the title compound was obtained as off white solid.

Workup

additionA mixture of 103 mg (0.41 mmol) of the
customThen, the solvent was evaporated i
customand the residue was chromatographed on SiO2 with a mixture of dichloromethane and tert.-butyl methyl ether (98:2

Sources & evidence

ORD record: ord-b27cc27c766f4f81bb7573dcfbb3180c
Source dataset: uspto-grants-2009_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07495001B2

Reaction notes

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