5-Benzyloxyindole → HCID 68283428, compound

HRID 1527263Notes

Reaction equation

HRID 1527263 reaction equation
[C:1]([O:5][C:6](=[O:28])[CH2:7][N:8]1[C:16]2[C:11](=[CH:12][C:13]([O:17]CC3C=CC=CC=3)=[CH:14][CH:15]=2)[C:10]([C:25](=[O:27])[CH3:26])=[CH:9]1)([CH3:4])([CH3:3])[CH3:2].C(OC1C=C2C(=CC=1)NC=C2)C1C=CC=CC=1>C(Cl)Cl.CO.[Pd]>[C:1]([O:5][C:6](=[O:28])[CH2:7][N:8]1[C:16]2[C:11](=[CH:12][C:13]([OH:17])=[CH:14][CH:15]=2)[C:10]([C:25](=[O:27])[CH3:26])=[CH:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 146245-BenzyloxyindoleHCID 68284065HCID 68284065, compound

Product 1

HCID 68283428HCID 68283428, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21226129Dichloromethane methanolSolvent

Procedure

To a solution of (3-acetyl-5-benzyloxy-indol-1-yl)-acetic acid tert-butyl ester (MS: 380.0 [M+H]+; tR (HPLC conditions c): 5.72 min; prepared from 5-benzyloxy-1H-indole [1215-59-4] in a similar manner as described in Scheme A13 (step A and B)) (3.3 g, 8.70 mmol) in CH2Cl2/MeOH (80 mL) was added Pd/C (0.093 g, 0.870 mmol). The reaction mixture was stirred at RT for 5 h under H2 atmosphere. The reaction mixture was filtered over a pad of Celite and washed with CH2Cl2 and MeOH. Volatiles were evaporated, and the crude mixture was purified by flash chromatography on silica gel (gradient c-hexane/EtOAc 2:1 to 100% EtOAc). TLC, Rf (c-hexane/EtOAc 1:1)=0.35; MS: 312.0 [M+Na]+; tR (HPLC conditions c): 4.27 min.

Workup

  1. custom5.72 min
  2. filtrationThe reaction mixture was filtered over a pad of Celite
  3. washwashed with CH2Cl2 and MeOH
  4. customVolatiles were evaporated
  5. customthe crude mixture was purified by flash chromatography on silica gel (gradient c-hexane/EtOAc 2:1 to 100% EtOAc)
  6. custom4.27 min.

Sources & evidence

ORD record
ord-d815ddfc2c544864845d46550a40571d
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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