Methanol → HCID 15766642, compound

HRID 1464575Notes

Reaction equation

HRID 1464575 reaction equation
[Cl:1][C:2]1[CH:21]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:19]=[C:18]([F:26])[C:3]=1[O:4][C:5]1[CH:13]=[C:12]2[C:8]([CH:9]=[N:10][N:11]2[CH2:14][C:15]([OH:17])=[O:16])=[CH:7][CH:6]=1.CO.[CH:29]1(N=C=NC2CCCCC2)CCCCC1>ClCCl.CN(C1C=CN=CC=1)C>[Cl:1][C:2]1[CH:21]=[C:20]([C:22]([F:23])([F:24])[F:25])[CH:19]=[C:18]([F:26])[C:3]=1[O:4][C:5]1[CH:13]=[C:12]2[C:8]([CH:9]=[N:10][N:11]2[CH2:14][C:15]([O:17][CH3:29])=[O:16])=[CH:7][CH:6]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 10868DicyclohexylcarbodiimideHCID 19086713HCID 19086713, compound

Product 1

HCID 15766642HCID 15766642, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

6-(2-Chloro-6-fluoro-4-trifluoromethylphenoxy)-indazol-1-ylacetic acid prepared as described in Example 3 (0.319 g) was suspended in dry dichloromethane (6 cm3) and methanol (0.04 cm3) and DMAP (10 mg) added. Dicyclohexylcarbodiimide (0.169 g) was added and the mixture stirred at room temperature for 2 hours and left to stand overnight. The mixture was filtered and the solvent removed from the filtrate under vacuum. The residue was purified by flash chromatography (hexane: TMBE,3:2) to yield methyl 2-[6-(2-chloro-6-fluoro-4-trifluoromethylphenoxy)indazol-1-yl]acetate (0.28 g) as an oil which solidified on standing.

Workup

  1. waitleft
  2. waitto stand overnight
  3. filtrationThe mixture was filtered
  4. customthe solvent removed from the filtrate under vacuum
  5. customThe residue was purified by flash chromatography (hexane: TMBE,3:2)

Sources & evidence

ORD record
ord-65de9ca25980429ea717545fa437c79a
Source dataset
uspto-grants-1994_04
Patent number
US05306692

Reaction notes

Loading…