Cesium carbonate → HCID 69641977, compound

HRID 890425Notes

Reaction equation

HRID 890425 reaction equation
Cl[CH2:2][C:3]1[C:4]([CH3:19])=[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.[CH2:20]([O:22][C:23](=[O:35])[CH2:24][N:25]1[C:33]2[C:28](=[CH:29][C:30]([OH:34])=[CH:31][CH:32]=2)[CH:27]=[CH:26]1)[CH3:21].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[CH2:20]([O:22][C:23](=[O:35])[CH2:24][N:25]1[C:33]2[C:28](=[CH:29][C:30]([O:34][CH2:2][C:3]3[C:4]([CH3:19])=[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:31][CH:32]=2)[CH:27]=[CH:26]1)[CH3:21]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 21935918HCID 21935918, compoundHCID 57675474(5-Hydroxy-indol-1-yl)-acetic acid ethyl ester

Product 1

HCID 69641977HCID 69641977, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 300 mg (0.94 mmol) 5-chloromethyl-4-methyl-2-(4-trifluoromethyl-phenyl)-pyrimidine and 206 mg (0.94 mmol) (5-hydroxy-indol-1-yl)-acetic acid ethyl ester (example 1 c]) in 3 ml DMF was added 375 mg (1.15 mmol) cesium carbonate. The reaction mixture was stirred for 3 h at RT and then partitioned between ether and water. The crude product was purified by chromatography over silica gel with AcOEt/heptane 1.2 to give 194 mg of pure {5-[4-Methyl-2-(4-trifluoromethyl-phenyl)-pyrimidin-5-ylmethoxy]-indol-1-yl}-acetic acid ethyl ester.

Workup

  1. custompartitioned between ether and water
  2. customThe crude product was purified by chromatography over silica gel with AcOEt/heptane 1.2

Sources & evidence

ORD record
ord-7ce72b77f26949bc83ff5e2da80156e0
Source dataset
uspto-grants-2006_02
Patent number
US06995263B2

Reaction notes

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