Methyl iodide → HCID 89599944, compound

HRID 1772175Notes

Reaction equation

HRID 1772175 reaction equation
[H-].[Na+].[Br:3][C:4]1[C:5]2[NH:12][CH:11]=[CH:10][C:6]=2[CH:7]=[N:8][CH:9]=1.[CH3:13]I>CN(C=O)C.C(Cl)Cl>[Br:3][C:4]1[C:5]2[N:12]([CH3:13])[CH:11]=[CH:10][C:6]=2[CH:7]=[N:8][CH:9]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 447212997-Bromo-1H-pyrrolo[3,2-c]pyridine

Product 1

HCID 89599944HCID 89599944, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

Sodium hydride (0.25 g, 6.2 mmol) is added under ice bath cooling to a mixture of 7-bromo-1H-pyrrolo[3,2-c]pyridine (0.8 g, 4.1 mmol) in DMF (10 ml). The mixture is stirred for 30 minutes before methyl iodide (0.25 ml, 4.1 mmol) is added. The mixture is warmed to RT and stirred for 17 h. The mixture is diluted with DCM and extracted with a saturated aqueous sodium hydrogencarbonate solution. The combined organic layers are dried over MgSO4 and concentrated in vacuo. The product is purified by RP HPLC. Yield: 0.61 g (71%). HPLC-MS: tR=0.88 min (METHOD—1).

Workup

  1. additionis added
  2. extractionextracted with a saturated aqueous sodium hydrogencarbonate solution
  3. dry with materialThe combined organic layers are dried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe product is purified by RP HPLC

Sources & evidence

ORD record
ord-5967e300fcc941bb980399e0b7489c1c
Source dataset
uspto-grants-2016_02
Patent number
US09249151B2

Reaction notes

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