Ethyl 5-(benzyloxy)-3-(2-isopropylphenyl)-1-(3-(naphthalen-1-yloxy)propyl)-1h-indole-2-carboxylate → Ethyl 5-hydroxy-3-(2-isopropylphenyl)-1-(3-(naphthalen-1-yloxy)propyl)-1h-indole-2-carboxylate

HRID 533272Notes

Reaction equation

HRID 533272 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([CH2:18][CH2:19][CH2:20][O:21][C:22]1[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH:25]=[CH:24][CH:23]=1)[C:13]([C:32]([O:34][CH2:35][CH3:36])=[O:33])=[C:12]2[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=1[CH:43]([CH3:45])[CH3:44])C1C=CC=CC=1>O1CCCC1.O[Pd]O>[OH:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([CH2:18][CH2:19][CH2:20][O:21][C:22]1[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH:25]=[CH:24][CH:23]=1)[C:13]([C:32]([O:34][CH2:35][CH3:36])=[O:33])=[C:12]2[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=1[CH:43]([CH3:44])[CH3:45]

Participants

4

Reactant 1

HCID 67316990Ethyl 5-(benzyloxy)-3-(2-isopropylphenyl)-1-(3-(naphthalen-1-yloxy)propyl)-1h-indole-2-carboxylate

Product 1

HCID 67316919Ethyl 5-hydroxy-3-(2-isopropylphenyl)-1-(3-(naphthalen-1-yloxy)propyl)-1h-indole-2-carboxylate

Reagents, catalysts & solvents 2

HCID 178526213HCID 178526213, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of EXAMPLE 149A (250 mg) and dihydroxypalladium (on carbon) (20 mg) in tetrahydrofuran was stirred a room temperature under a hydrogen atmosphere (30 psi) for 29 hours. The insoluble material was filtered off and the filtrate was concentrated. The residue was purified by flash chromatography, eluting with dichloromethane to provide the title compound.

Workup

  1. filtrationThe insoluble material was filtered off
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified by flash chromatography
  4. washeluting with dichloromethane

Sources & evidence

ORD record
ord-56dee2d3924d4f93a7a233dc31a11616
Source dataset
uspto-grants-2014_10
Patent number
US08853209B2

Reaction notes

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