(1-Bromoethyl)benzene → methyl 2-methyl-1-(1-phenylethyl)-1H-pyrrolo[2,3-c]pyridine-3-carboxylate

HRID 2206603Notes

Reaction equation

HRID 2206603 reaction equation
[CH3:1][C:2]1[NH:10][C:5]2=[CH:6][N:7]=[CH:8][CH:9]=[C:4]2[C:3]=1[C:11]([O:13][CH3:14])=[O:12].[H-].[Na+].Br[CH:18]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH3:19].[NH4+].[Cl-]>CN(C)C=O>[CH3:1][C:2]1[N:10]([CH:18]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH3:19])[C:5]2=[CH:6][N:7]=[CH:8][CH:9]=[C:4]2[C:3]=1[C:11]([O:13][CH3:14])=[O:12]

Participants

6

Reactant 4

HCID 11454(1-Bromoethyl)benzeneHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 89739208Methyl 2-methyl-1H-pyrrolo[2,3-c]pyridine-3-carboxylate

Product 1

HCID 89740401methyl 2-methyl-1-(1-phenylethyl)-1H-pyrrolo[2,3-c]pyridine-3-carboxylateYield 94%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of methyl 2-methyl-1H-pyrrolo[2,3-c]pyridine-3-carboxylate (550 mg, 2.89 mmol) and sodium hydride (200 mg, 4.34 mmol) in N,N-dimethylformamide (3.0 mL) was stirred at room temperature for 0.5 hour, and then (1-bromoethyl)benzene (589 mg, 3.18 mmol) was added. The mixture was stirred at room temperature for 3 hours. The reaction mixture was poured into saturated NH4Cl and extracted with ethyl acetate. Organic layers were combined and concentrated to give a residue. The residue was purified by chromatography (petroleum ether/ethyl acetate=5:1) to give methyl 2-methyl-1-(1-phenylethyl)-1H-pyrrolo[2,3-c]pyridine-3-carboxylate (800 mg, 94%).

Workup

  1. stirringThe mixture was stirred at room temperature for 3 hours
  2. extractionextracted with ethyl acetate
  3. concentrationconcentrated
  4. customto give a residue
  5. customThe residue was purified by chromatography (petroleum ether/ethyl acetate=5:1)

Sources & evidence

ORD record
ord-59906072d7cb42d5a287ad95c76a4574
Source dataset
uspto-grants-2016_06
Patent number
US09371331B2

Reaction notes

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