Water → HCID 58306833, compound

HRID 1909856Notes

Reaction equation

HRID 1909856 reaction equation
C[C:2]1[N:3]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=2)[C:4]2[C:9]([CH:10]=1)=[CH:8][C:7](Br)=[CH:6][C:5]=2[C:12](O)=O.CB1OB(C)OB(C)O1.[C:32](=[O:35])([O-])[O-].[K+].[K+].O1CCOC[CH2:39]1.[OH2:44]>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Cl:22][C:19]1[CH:18]=[CH:17][C:16]([CH2:15][N:3]2[C:4]3[C:9](=[CH:8][C:7]([CH3:39])=[CH:6][C:5]=3[C:12]([O:35][CH3:32])=[O:44])[CH:10]=[CH:2]2)=[CH:21][CH:20]=1

Participants

7

Reactant 5

HCID 962WaterHCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 574072TrimethylboroxineHCID 66868081HCID 66868081, compound

Product 1

HCID 58306833HCID 58306833, compound

Reagents, catalysts & solvents 1

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalyst

Procedure

To a mixture of methyl 5-bromo-1-(4-chlorobenzyl)-1H-indole-7-carboxylic acid (300 mg), trimethylboroxin (100 mg), potassium carbonate (165 mg), and 1,4-dioxane (9 mL) was added tetrakis(triphenylphosphine) palladium (0) (46 mg) at room temperature. This mixture was stirred under heating with reflux for 15 hours. The reaction mixture was left to be cooled to room temperature, and water was added thereto, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, the solvent was evaporated, and the obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate) to obtain methyl 1-(4-chlorobenzyl)-5-methyl-1H-indole-7-carboxylate (60 mg).

Workup

  1. temperatureunder heating
  2. temperaturewith reflux for 15 hours
  3. waitThe reaction mixture was left
  4. extractionfollowed by extraction with ethyl acetate
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. customthe solvent was evaporated
  7. customthe obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-d05940da20204beda3d5e027c21a624f
Source dataset
uspto-grants-2013_12
Patent number
US08598355B2

Reaction notes

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