Methanol → 3-(1-(4-fluorophenyl)-1H-indazol-5-yl)-2,2,5-trimethylhexanoic acid

HRID 218128Notes

Reaction equation

HRID 218128 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([CH:17]([CH2:25][CH:26]([CH3:28])[CH3:27])[C:18]([CH3:24])([CH3:23])[C:19]([O:21]C)=[O:20])=[CH:14][CH:15]=3)[CH:10]=[N:9]2)=[CH:4][CH:3]=1.[OH-].[Na+].CO>CS(C)=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([CH:17]([CH2:25][CH:26]([CH3:28])[CH3:27])[C:18]([CH3:23])([CH3:24])[C:19]([OH:21])=[O:20])=[CH:14][CH:15]=3)[CH:10]=[N:9]2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 59251058methyl 3-(1-(4-fluorophenyl)-1H-indazol-5-yl)-2,2,5-trimethylhexanoate

Product 1

HCID 670054443-(1-(4-fluorophenyl)-1H-indazol-5-yl)-2,2,5-trimethylhexanoic acid

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Methyl 3-(1-(4-fluorophenyl)-1H-indazol-5-yl)-2,2,5-trimethylhexanoate (0.4 mmol) was dissolved in 5 mL of DMSO, 10 mL of 1 NaOH and 5 mL of MeOH and heated at 100° C. overnight. The reaction was quenched with sat. KH2PO4 and extracted with 2× EtOAc. The EtOAc extracts were dried over MgSO4, filtered, and concentrated by rotary evaporator to give 3-(1-(4-fluorophenyl)-1H-indazol-5-yl)-2,2,5-trimethylhexanoic acid. MS found: (M+H)+=369.

Workup

  1. customThe reaction was quenched with sat. KH2PO4
  2. extractionextracted with 2× EtOAc
  3. dry with materialThe EtOAc extracts were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated by rotary evaporator

Sources & evidence

ORD record
ord-d8fdc2f708924535b64544bda61e0a15
Source dataset
uspto-grants-2012_06
Patent number
US08198311B2

Reaction notes

Loading…