HCID 22627300, compound → HCID 22627166, compound

HRID 1108726Notes

Reaction equation

HRID 1108726 reaction equation
[C:1]([C:4]1[C:12]2[C:7](=[CH:8][C:9]([C:13]([O:15][CH3:16])=[O:14])=[CH:10][CH:11]=2)[N:6]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[Cl:24])[C:5]=1[CH2:25][CH3:26])(=O)[CH3:2]>O1CCCC1>[Cl:24][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[CH2:17][N:6]1[C:7]2[C:12](=[CH:11][CH:10]=[C:9]([C:13]([O:15][CH3:16])=[O:14])[CH:8]=2)[C:4]([CH2:1][CH3:2])=[C:5]1[CH2:25][CH3:26]

Participants

3

Reactant 1

HCID 22627300HCID 22627300, compound

Product 1

HCID 22627166HCID 22627166, compoundYield 39.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
20 °C

Procedure

To a solution of methyl 3-acetyl-1-(2-chlorobenzyl)-2-ethylindole-6-carboxylate (110 mg) in tetrahydrofuran (5 ml) was added 1M solution of boran in tetrahydrofuran (0.6 ml) in one portion at 0° C. The mixture was stirred at 20° C. for 1 hour, then quenched with water and extracted with ethyl acetate. The organic phase was washed with brine, dried over magnesium sulfate and evaporated in vacuo. The residue was chromatographed on silica gel eluting with a mixture of hexane and ethyl acetate (2:1) to give methyl 1-(2-chlorobenzyl)-2,3-diethylindole-6-carboxylate (42 mg) as colorless crystals.

Workup

  1. customquenched with water
  2. extractionextracted with ethyl acetate
  3. washThe organic phase was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo
  6. customThe residue was chromatographed on silica gel eluting with a mixture of hexane and ethyl acetate (2:1)

Sources & evidence

ORD record
ord-ea59227f2cec4765a38bfd8e7affb9e2
Source dataset
uspto-grants-2000_05
Patent number
US06069156

Reaction notes

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