Benzoyl chloride → HCID 89739132, compound

HRID 1527002Notes

Reaction equation

HRID 1527002 reaction equation
[H-].[Na+].[CH3:3][C:4]1[NH:5][C:6]2[C:11]([C:12]=1[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[CH:10][CH:9]=[CH:8][CH:7]=2.[C:20](Cl)(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>O1CCCC1>[C:20]([N:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:12]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[C:4]1[CH3:3])(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 24758Sodium hydrideHCID 80156864HCID 80156864, compound

Product 1

HCID 89739132HCID 89739132, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of sodium hydride (73 mg, w/w=60%, 1.8 mmol) tert-butyl 2-methyl-1H-indole-3-carboxylate (350 mg, 1.5 mmol) in tetrahydrofuran (30 mL) was added benzoyl chloride (250 mg, 1.8 mmol). The reaction solution was stirred at room temperature for 12 hours. The mixture was concentrated to give a residue, which was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=3:1) to give tert-butyl 1-benzoyl-2-methyl-1H-indole-3-carboxylate (440 mg, 88%).

Workup

  1. concentrationThe mixture was concentrated
  2. customto give a residue, which
  3. customwas purified by column chromatography (silica gel, petroleum ether/ethyl acetate=3:1)

Sources & evidence

ORD record
ord-03bdb811d531426ca4ef2bd705a4a20e
Source dataset
uspto-grants-2015_07
Patent number
US09085583B2

Reaction notes

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