HCID 24753616, compound → HCID 24753617, compound

HRID 420811Notes

Reaction equation

HRID 420811 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([OH:17])=[CH:14][CH:15]=2)[C:10]([C:18](=[O:29])/[CH:19]=[CH:20]/[C:21]2[CH:26]=[CH:25][C:24]([F:27])=[C:23]([F:28])[CH:22]=2)=[C:9]1[CH:30]([CH3:32])[CH3:31])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CO.[Pd]>[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([OH:17])=[CH:14][CH:15]=2)[C:10]([C:18](=[O:29])[CH2:19][CH2:20][C:21]2[CH:26]=[CH:25][C:24]([F:27])=[C:23]([F:28])[CH:22]=2)=[C:9]1[CH:30]([CH3:32])[CH3:31])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 24753616HCID 24753616, compound2×

Product 1

HCID 24753617HCID 24753617, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

General Procedure H. To a solution of (E)-1-(1-benzyl-5-hydroxy-2-isopropyl-1H-indol-3-yl)-3-(3,4-difluorophenyl)prop-2-en-1-one (Compound 30, 25 mg, 0.058 mmol) in MeOH (2.0 ml) was added Pd—C (10%, 3.0 mg, 0.0029 mmol). The suspension was stirred under an atmosphere of hydrogen gas (1 atm) at room temperature for 2 h. The mixture was filtered through a pad of silica gel and concentrated. The residue was purified by PTLC (30% EtOAc-hexanes) to yield 1-(1-benzyl-5-hydroxy-2-isopropyl-1H-indol-3-yl)-3-(3,4-difluorophenyl)propan-1-one (Compound 31) as a light yellow solid.

Workup

  1. filtrationThe mixture was filtered through a pad of silica gel
  2. concentrationconcentrated
  3. customThe residue was purified by PTLC (30% EtOAc-hexanes)

Sources & evidence

ORD record
ord-03517a2e8b0844b2bb7e2ac12169d5e5
Source dataset
uspto-grants-2012_01
Patent number
US08097644B2

Reaction notes

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