Lithium Hydroxide → HCID 11408074, compound

HRID 890426Notes

Reaction equation

HRID 890426 reaction equation
C([O:3][C:4](=[O:34])[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][C:11]([O:15][CH2:16][C:17]3[C:18]([CH3:33])=[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.CCOCC>[CH3:33][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:34])=[O:3])[CH:7]=[CH:8]3)=[CH:22][N:21]=[C:20]([C:23]2[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:30])[F:31])=[CH:25][CH:24]=2)[N:19]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 69641977HCID 69641977, compound

Product 1

HCID 11408074HCID 11408074, compoundYield 82.7%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

175 mg (0.37 mmol) {5-[4-methyl-2-(4-trifluoromethyl-phenyl)-pyrimidin-5-ylmethoxy]-indol-1-yl}-acetic acid ethyl ester and 0.75 ml 1N lithium hydroxide solution were stirred in 2 ml THF at RT for 2 h. The reaction mixture was taken up in ether and washed with 1N HCl and water. The crude product was suspended in ether/heptane 1:19 and the resulting crystals were filtered off to give 135 mg of pure {5-[4-methyl-2-(4-trifluoromethyl-phenyl)-pyrimidin-5-ylmethoxy]-indol-1-yl}-acetic acid.

Workup

  1. washwashed with 1N HCl and water
  2. filtrationthe resulting crystals were filtered off

Sources & evidence

ORD record
ord-30ece1a9de804b5ba9141cf1e683d38b
Source dataset
uspto-grants-2006_02
Patent number
US06995263B2

Reaction notes

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