Cesium carbonate → {5-[4-(2-Methoxy-ethyl)-2-(4-trifluoromethyl-phenyl)-pyrimidin-5-ylmethoxy]-indol-1-yl}-acetic acid ethyl ester

HRID 890421Notes

Reaction equation

HRID 890421 reaction equation
Cl[CH2:2][C:3]1[C:4]([CH2:19][CH2:20][O:21][CH3:22])=[N:5][C:6]([C:9]2[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=2)=[N:7][CH:8]=1.[CH2:23]([O:25][C:26](=[O:38])[CH2:27][N:28]1[C:36]2[C:31](=[CH:32][C:33]([OH:37])=[CH:34][CH:35]=2)[CH:30]=[CH:29]1)[CH3:24].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.CCOCC>[CH2:23]([O:25][C:26](=[O:38])[CH2:27][N:28]1[C:36]2[C:31](=[CH:32][C:33]([O:37][CH2:2][C:3]3[C:4]([CH2:19][CH2:20][O:21][CH3:22])=[N:5][C:6]([C:9]4[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=4)=[N:7][CH:8]=3)=[CH:34][CH:35]=2)[CH:30]=[CH:29]1)[CH3:24]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 219356255-Chloromethyl-4-(2-methoxy-ethyl)-2-(4-trifluoromethyl-phenyl)-pyrimidineHCID 57675474(5-Hydroxy-indol-1-yl)-acetic acid ethyl ester

Product 1

HCID 69641981{5-[4-(2-Methoxy-ethyl)-2-(4-trifluoromethyl-phenyl)-pyrimidin-5-ylmethoxy]-indol-1-yl}-acetic acid ethyl esterYield 32.5%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 300 mg (0.91 mmol) 5-chloromethyl-4-(2-methoxy-ethyl)-2-(4-trifluoromethyl-phenyl)-pyrimidine and 199 mg (0.91 mmol) (5-hydroxy-indol-1-yl)-acetic acid ethyl ester in 5 ml DMF was added 443 mg (136 mmol) cesium carbonate. The reaction mixture was stirred at RT for 3 h and then taken up in ether, washed with 1N HCl and water. The crude product was purified by chromatography with AcOEt/heptane 1:4 to provide 152 mg of pure {5-[4-(2-methoxy-ethyl)-2-(4-trifluoromethyl-phenyl)-pyrimidin-5-ylmethoxy]-indol-1-yl}-acetic acid ethyl ester.

Workup

  1. washwashed with 1N HCl and water
  2. customThe crude product was purified by chromatography with AcOEt/heptane 1:4

Sources & evidence

ORD record
ord-ef3a3e40906848679717796d9d850a0b
Source dataset
uspto-grants-2006_02
Patent number
US06995263B2

Reaction notes

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