Methyl iodide → 6-Bromo-1-methyl-1H-pyrrolo[2,3-b]pyridine

HRID 1051487Notes

Reaction equation

HRID 1051487 reaction equation
[Br:1][C:2]1[N:7]=[C:6]2[NH:8][CH:9]=[CH:10][C:5]2=[CH:4][CH:3]=1.[H-].[Na+].[CH3:13]I>CN(C=O)C>[Br:1][C:2]1[N:7]=[C:6]2[N:8]([CH3:13])[CH:9]=[CH:10][C:5]2=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 111599156-Bromo-7-azaindole

Product 1

HCID 867292686-Bromo-1-methyl-1H-pyrrolo[2,3-b]pyridineYield 37.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 6-bromo-1H-pyrrolo[2,3-b]pyridine (500 mg, 2.55 mmol) in DMF (10 mL) was added NaH (306 mg, 7.65 mmol, m %/60%). The mixture was stirred at room temperature for 1 h and then MeI (398 mg, 2.8 mmol) was added. The reaction mixture was then stirred at room temperature for 4 h after which, TLC showed the completion of the reaction. The reaction mixture was quenched by addition of water and then extracted with EtOAc. Combined organic layers were concentrated and the residue was purified by Prep-TLC (PE:EA=5:1) to give the desired product (200 mg) which was used directly in the next step.

Workup

  1. stirringThe reaction mixture was then stirred at room temperature for 4 h after which, TLC
  2. customthe completion of the reaction
  3. customThe reaction mixture was quenched by addition of water
  4. extractionextracted with EtOAc
  5. concentrationCombined organic layers were concentrated
  6. customthe residue was purified by Prep-TLC (PE:EA=5:1)

Sources & evidence

ORD record
ord-7e45ef7bef5a4b1b9ef255b972a15f03
Source dataset
uspto-grants-2016_07
Patent number
US09388173B2

Reaction notes

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