Sodium t-butoxide → Ethyl 3-(4-{[4-[5-fluoro-2-(methyloxy)phenyl]-2-hydroxy-4-methyl-2-(trifluoromethyl)pentyl]amino}-6-methyl-1H-indazol-1-yl)benzoate

HRID 418810Notes

Reaction equation

HRID 418810 reaction equation
CC(C)([O-])C.[Na+].[F:7][C:8]1[CH:9]=[CH:10][C:11]([O:52][CH3:53])=[C:12]([C:14]([CH3:51])([CH3:50])[CH2:15][C:16]([OH:49])([C:45]([F:48])([F:47])[F:46])[CH2:17][NH:18][C:19]2[CH:27]=[C:26]([CH3:28])[CH:25]=[C:24]3[C:20]=2[CH:21]=[N:22][N:23]3[C:29]2[CH:30]=[C:31]([CH:42]=[CH:43][CH:44]=2)[C:32]([O:34][CH2:35][C:36]2C=CC=CC=2)=[O:33])[CH:13]=1>C(O)C>[F:7][C:8]1[CH:9]=[CH:10][C:11]([O:52][CH3:53])=[C:12]([C:14]([CH3:50])([CH3:51])[CH2:15][C:16]([OH:49])([C:45]([F:46])([F:48])[F:47])[CH2:17][NH:18][C:19]2[CH:27]=[C:26]([CH3:28])[CH:25]=[C:24]3[C:20]=2[CH:21]=[N:22][N:23]3[C:29]2[CH:30]=[C:31]([CH:42]=[CH:43][CH:44]=2)[C:32]([O:34][CH2:35][CH3:36])=[O:33])[CH:13]=1

Participants

4

Reactant 2

HCID 23676156Sodium t-butoxideHCID 59010008phenylmethyl 3-(4-{[4-[5-fluoro-2-(methyloxy)phenyl]-2-hydroxy-4-methyl-2-(trifluoromethyl)pentyl]amino}-6-methyl-1H-indazol-1-yl)benzoate2×

Product 1

HCID 57615928Ethyl 3-(4-{[4-[5-fluoro-2-(methyloxy)phenyl]-2-hydroxy-4-methyl-2-(trifluoromethyl)pentyl]amino}-6-methyl-1H-indazol-1-yl)benzoateYield 58.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium tert-butoxide (4 mg, 0.042 mmol) was added to a solution of phenylmethyl 3-(4-{[4-[5-fluoro-2-(methyloxy)phenyl]-2-hydroxy-4-methyl-2-(trifluoromethyl)pentyl]amino}-6-methyl-1H-indazol-1-yl)benzoate (Intermediate 30, 23 mg, 0.035 mmol) in ethanol (3 mL) and the mixture stirred at room temperature for 75 min. The mixture was then partitioned between dichloromethane (20 mL) and aqueous ammonium chloride (20 mL). The organic layer was separated, passed through a hydrophobic frit and evaporated and the residue purified by mass-directed autopreparation to give the title compound (12 mg).

Workup

  1. customThe mixture was then partitioned between dichloromethane (20 mL) and aqueous ammonium chloride (20 mL)
  2. customThe organic layer was separated
  3. customevaporated
  4. customthe residue purified by mass-directed autopreparation

Sources & evidence

ORD record
ord-0f14e1f38af340e1b1cb498caa227a31
Source dataset
uspto-grants-2012_01
Patent number
US08093281B2

Reaction notes

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