Ethanol → HCID 66657649, compound

HRID 420968Notes

Reaction equation

HRID 420968 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:15][C:16]3[C:21]([C:22](=[O:24])[NH2:23])=[CH:20][CH:19]=[CH:18][N:17]=3)[CH:13]=2)[N:8]([C:25]2[CH:30]=[CH:29][C:28]([O:31][C:32]([F:35])([F:34])[F:33])=[CH:27][CH:26]=2)[C:7]=1[CH2:36][C:37]([O:39]CC)=[O:38])=[O:5])[CH3:2].[OH-].[Na+].CCO>O>[CH2:1]([O:3][C:4]([C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:15][C:16]3[C:21]([C:22](=[O:24])[NH2:23])=[CH:20][CH:19]=[CH:18][N:17]=3)[CH:13]=2)[N:8]([C:25]2[CH:30]=[CH:29][C:28]([O:31][C:32]([F:35])([F:34])[F:33])=[CH:27][CH:26]=2)[C:7]=1[CH2:36][C:37]([OH:39])=[O:38])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 66657657HCID 66657657, compound

Product 1

HCID 66657649HCID 66657649, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
55 °C

Procedure

A mixture of 5-(3-carbamoylpyridin-2-yl-oxy)-2-ethoxycarbonylmethyl-1-(4-trifluoromethoxy-phenyl)indole-3-carboxylic acid ethyl ester (86 mg, 0.15 mmol, see step (a) above), NaOH (aq, 1M, 0.45 mL), EtOH (1 mL) and H2O (1 mL) was stirred at 55° C. for 3 h, cooled, filtered through Celite® and acidified to pH 4 with HCl (aq, 2M). The solid was filtered off, washed with H2O and purified by chromatography and recrystallisation from EtOAc. Yield 36 mg (46%), mp 128-130° C.

Workup

  1. temperaturecooled
  2. filtrationfiltered through Celite®
  3. filtrationThe solid was filtered off
  4. washwashed with H2O
  5. custompurified by chromatography and recrystallisation from EtOAc

Sources & evidence

ORD record
ord-b9bc912df59a42dfbcd9c5abda07c220
Source dataset
uspto-grants-2012_01
Patent number
US08097623B2

Reaction notes

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