HCID 22933600, compound → HCID 22933604, compound

HRID 1269994Notes

Reaction equation

HRID 1269994 reaction equation
[C:1](C=P(CCCC)(CCCC)CCCC)#N.C1(C)C=CC=CC=1.[CH2:24]([C:26]1[C:34]([OH:35])=[CH:33][CH:32]=[C:31]2[C:27]=1[CH:28]=[N:29][NH:30]2)[CH3:25]>C1(C)C=CC=CC=1>[CH:24]([C:26]1[C:34]([OH:35])=[CH:33][CH:32]=[C:31]2[C:27]=1[CH:28]=[N:29][NH:30]2)([CH3:1])[CH3:25]

Participants

4

Reactant 2

HCID 22933600HCID 22933600, compoundHCID 86760483HCID 86760483, compound

Product 1

HCID 22933604HCID 22933604, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A cyanomethylenetributylphosphorane/toluene solution (1.2 g, 4.53 mmol) was added to a solution prepared by dissolving the 4-ethyl-1H-indazol-5-ol (359 mg, 1.46 mmol) obtained in Example 682 and the cis-2-(4-hydroxycyclohexyl)-1H-isoinzole-1,3(2H)-dione (854 mg, 3.48 mmol) obtained in Example 323, (c) in toluene (15 ml), and the resulting mixture was stirred at 120° C. for 3 hours. The reaction solution was concentrated, and to the resulting residue were added chloroform and a 1N-aqueous sodium hydroxide solution to effect partition, followed by extraction with chloroform (twice). The extract solution was dried over anhydrous magnesium sulfate. The residue was purified by a silica gel chromatography (hexane/ethyl acetate=2/1) to obtain trans-2-{4-[(4-ethyl-1H-indazol-5-yl)oxy]cyclohexyl}-1H-isoindole-1,3(2H)-dione (681.1 mg, 50%).

Workup

  1. customprepared

Sources & evidence

ORD record
ord-4639f4f4e744484ba5d01cb852c914a2
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

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