Lithium Hydroxide → HCID 11248727, compound

HRID 890422

Reaction equation

HRID 890422 reaction equation
C([O:3][C:4](=[O:37])[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][C:11]([O:15][CH2:16][C:17]3[C:18]([CH2:33][CH2:34][O:35][CH3:36])=[N:19][C:20]([C:23]4[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][CH:24]=4)=[N:21][CH:22]=3)=[CH:12][CH:13]=2)[CH:8]=[CH:7]1)C.[OH-].[Li+]>C1COCC1>[CH3:36][O:35][CH2:34][CH2:33][C:18]1[C:17]([CH2:16][O:15][C:11]2[CH:10]=[C:9]3[C:14](=[CH:13][CH:12]=2)[N:6]([CH2:5][C:4]([OH:37])=[O:3])[CH:7]=[CH:8]3)=[CH:22][N:21]=[C:20]([C:23]2[CH:24]=[CH:25][C:26]([C:29]([F:32])([F:30])[F:31])=[CH:27][CH:28]=2)[N:19]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 69641981{5-[4-(2-Methoxy-ethyl)-2-(4-trifluoromethyl-phenyl)-pyrimidin-5-ylmethoxy]-indol-1-yl}-acetic acid ethyl ester

Product 1

HCID 11248727HCID 11248727, compoundYield 83.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 147 mg (0.29 mmol) {5-[4-(2-methoxy-ethyl)-2-(4-trifluoromethyl-phenyl)-pyrimidin-5-ylmethoxy]-indol-1-yl}-acetic acid ethyl ester and 0.9 ml 1N lithium hydroxide solution in 1.5 ml THF were stirred over night at RT. The reaction mixture was partitioned between ether, 1N HCl and water. The residue was suspended in ether/heptane 1:9 and the resulting crystals were filtered off to give 118 mg of pure {5-[4-(2-methoxy-ethyl)-2-(4-trifluoromethyl-phenyl)-pyrimidin-5-ylmethoxy]-indol-1-yl}-acetic acid.

Workup

  1. customThe reaction mixture was partitioned between ether, 1N HCl and water
  2. filtrationthe resulting crystals were filtered off

Sources & evidence

ORD record
ord-ef39872262c04ab39c24eb4b6e9b641b
Source dataset
uspto-grants-2006_02
Patent number
US06995263B2

Linked notes

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