Toluene → 1,1,1-Trifluoro-4-(3-fluoro-2-methoxyphenyl)-2-[(1H-indazol-4-yl)iminomethyl]-4-methylpentan-2-ol

HRID 1443132Notes

Reaction equation

HRID 1443132 reaction equation
[F:1][C:2]1[C:3]([O:20][CH3:21])=[C:4]([C:8]([CH3:19])([CH3:18])[CH2:9][C:10]([OH:17])([C:13]([F:16])([F:15])[F:14])[CH:11]=O)[CH:5]=[CH:6][CH:7]=1.[NH2:22][C:23]1[CH:31]=[CH:30][CH:29]=[C:28]2[C:24]=1[CH:25]=[N:26][NH:27]2.C1(C)C=CC=CC=1>C(O)(=O)C>[F:16][C:13]([F:14])([F:15])[C:10]([CH:11]=[N:22][C:23]1[CH:31]=[CH:30][CH:29]=[C:28]2[C:24]=1[CH:25]=[N:26][NH:27]2)([OH:17])[CH2:9][C:8]([C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[C:3]=1[O:20][CH3:21])([CH3:18])[CH3:19]

Participants

5

Reactant 3

HCID 1140TolueneHCID 413085NoName_3327HCID 179890864-(3-Fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentanal

Product 1

HCID 179892531,1,1-Trifluoro-4-(3-fluoro-2-methoxyphenyl)-2-[(1H-indazol-4-yl)iminomethyl]-4-methylpentan-2-olYield 73.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

1.46 g (4.746 mmol) of 4-(3-fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)-pentanal is stirred with 632 mg (4.746 mmol) of 4-aminoindazole in 6.78 ml of glacial acetic acid for two days at room temperature. The reaction mixture is drawn off three times with toluene in a rotary evaporator, and the residue is chromatographed on silica gel (mobile solvent:ethyl acetate/hexane). 1.47 g (73.5%) of the desired compound is isolated.

Workup

  1. customin a rotary evaporator
  2. customthe residue is chromatographed on silica gel (mobile solvent:ethyl acetate/hexane)

Sources & evidence

ORD record
ord-1de148660aa54a758e18cf59945b121e
Source dataset
uspto-grants-2010_02
Patent number
US07659297B2

Reaction notes

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