Benzyl Bromide → 1-Benzyl-2-isopropyl-5-methoxy-1H-pyrrolo[2,3-c]pyridine-3-carbaldehyde

HRID 43264Notes

Reaction equation

HRID 43264 reaction equation
[CH:1]([C:4]1[NH:14][C:7]2=[CH:8][N:9]=[C:10]([O:12][CH3:13])[CH:11]=[C:6]2[C:5]=1[CH:15]=[O:16])([CH3:3])[CH3:2].[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH2:17]([N:14]1[C:7]2=[CH:8][N:9]=[C:10]([O:12][CH3:13])[CH:11]=[C:6]2[C:5]([CH:15]=[O:16])=[C:4]1[CH:1]([CH3:3])[CH3:2])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 446084482-isopropyl-5-methoxy-1H-pyrrolo[2,3-c]pyridine-3-carbaldehyde2×

Product 1

HCID 446084491-Benzyl-2-isopropyl-5-methoxy-1H-pyrrolo[2,3-c]pyridine-3-carbaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-isopropyl-5-methoxy-1H-pyrrolo[2,3-c]pyridine-3-carbaldehyde (Compound 6, 110 mg, 0.50 mmol), benzyl bromide (0.18 ml, 1.50 mmol), and K2CO3 (208 mg, 1.50 mmol) in DMF (2.5 ml) was stirred at room temperature for 4 h. The solvent was removed in vacuo and the residue was purified by chromatography on silica gel (50% EtOAc-hexanes) to yield the title compound as yellow solid.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was purified by chromatography on silica gel (50% EtOAc-hexanes)

Sources & evidence

ORD record
ord-8afd41bac0894c759f9991c2cde4b0a8
Source dataset
uspto-grants-2013_09
Patent number
US08536339B2

Reaction notes

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