HCID 49787370, compound → HCID 24753518, compound

HRID 420809Notes

Reaction equation

HRID 420809 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)=[O:19])=[C:9]1[CH:21]([CH3:23])[CH3:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:24][Li]>>[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:19])[CH3:24])=[C:9]1[CH:21]([CH3:23])[CH3:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 49787370HCID 49787370, compound2×HCID 178418348HCID 178418348, compound

Product 1

HCID 24753518HCID 24753518, compound

Procedure

General Procedure F. To a solution of 1-benzyl-5-hydroxy-2-isopropyl-1H-indole-3-carboxylic acid (Compound 28, 242 mg, 0.78 mmol) under argon was added methyllithium (3.0 M in diethoxymethane, 5.2 ml, 15.7 mmol) at room temperature. The reaction was stirred for 4 h and was quenched with 1 M HCl, extracted with EtOAc. The organic layer was washed with brine, dried over Na2SO4, and concentrated. The residue was purified by flash chromatography on silica gel eluting with 0-50% EtOAc-hexanes to yield 1-(1-benzyl-5-hydroxy-2-isopropyl-1H-indol-3-yl)ethanone (Compound 29) as a yellow solid.

Workup

  1. customwas quenched with 1 M HCl
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography on silica gel eluting with 0-50% EtOAc-hexanes

Sources & evidence

ORD record
ord-623f0129c5bd45a790738f5c21667a87
Source dataset
uspto-grants-2012_01
Patent number
US08097644B2

Reaction notes

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