Boron → HCID 22627166, compound

HRID 278111Notes

Reaction equation

HRID 278111 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].[B]>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

4

Reactant 2

HCID 5462311BoronHCID 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 boron 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 chase was washed with brine, dried over magnesium sulfate and evaporated in vacuo. The residue was chromatographed or 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 chase was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo
  6. customThe residue was chromatographed
  7. additionsilica gel eluting with a mixture of hexane and ethyl acetate (2:1)

Sources & evidence

ORD record
ord-bd3ba23f42fe4e63bafbf46412ca2ae2
Source dataset
uspto-grants-2002_03
Patent number
US06358992B1

Reaction notes

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