Potassium Iodide → {6-[4-(2-Methoxy-ethyl)-6-methyl-2-(4-trifluoromethyl-phenyl)-pyrimidin-5-ylmethoxy]-indol-1-yl}-acetic acid ethyl ester

HRID 890471Notes

Reaction equation

HRID 890471 reaction equation
[CH2:1]([O:3][C:4](=[O:16])[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([OH:15])[CH:13]=2)[CH:8]=[CH:7]1)[CH3:2].Cl[CH2:18][C:19]1[C:20]([CH2:36][CH2:37][O:38][CH3:39])=[N:21][C:22]([C:26]2[CH:31]=[CH:30][C:29]([C:32]([F:35])([F:34])[F:33])=[CH:28][CH:27]=2)=[N:23][C:24]=1[CH3:25].C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[K+]>C(#N)C>[CH2:1]([O:3][C:4](=[O:16])[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:15][CH2:18][C:19]3[C:20]([CH2:36][CH2:37][O:38][CH3:39])=[N:21][C:22]([C:26]4[CH:27]=[CH:28][C:29]([C:32]([F:35])([F:33])[F:34])=[CH:30][CH:31]=4)=[N:23][C:24]=3[CH3:25])[CH:13]=2)[CH:8]=[CH:7]1)[CH3:2]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 10796Cesium carbonateHCID 219357495-Chloromethyl-4-(2-methoxy-ethyl)-6-methyl-2-(4-trifluoromethyl-phenyl)-pyrimidineHCID 68821422(6-Hydroxy-indol-1-yl)-acetic acid ethyl ester

Product 1

HCID 69637739{6-[4-(2-Methoxy-ethyl)-6-methyl-2-(4-trifluoromethyl-phenyl)-pyrimidin-5-ylmethoxy]-indol-1-yl}-acetic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In analogy to the procedure described in example 7 a], (6-hydroxy-indol-1-yl)-acetic acid ethyl ester (example 6 b]) was reacted with 5-chloromethyl-4-(2-methoxy-ethyl)-6-methyl-2-(4-trifluoromethyl-phenyl)-pyrimidine in the presence of cesium carbonate and potassium iodide, using acetonitrile as solvent, to obtain the title compound as colorless crystals.

Sources & evidence

ORD record
ord-93e1569ebbc24625ad3176741c37fe16
Source dataset
uspto-grants-2006_02
Patent number
US06995263B2

Reaction notes

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