Water → 1H-Pyrrolo[2,3-b]pyridine, 6-fluoro-1-methyl-

HRID 1622875Notes

Reaction equation

HRID 1622875 reaction equation
[F:1][C:2]1[N:7]=[C:6]2[NH:8][CH:9]=[CH:10][C:5]2=[CH:4][CH:3]=1.[C:11](=O)([O-])[O-].[K+].[K+].CI.O>CN(C)C=O>[F:1][C:2]1[N:7]=[C:6]2[N:8]([CH3:11])[CH:9]=[CH:10][C:5]2=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 247288916-Fluoro-1H-pyrrolo(2,3-b)pyridine

Product 1

HCID 678165211H-Pyrrolo[2,3-b]pyridine, 6-fluoro-1-methyl-Yield 92.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 6-fluoro-1H-pyrrolo[2,3-b]pyridine (250 g, 1.84 mol) in dimethylformamide (2.50 L) is added potassium carbonate (507.6 g; 3.67 mol), followed by methyl iodide (171.6 mL, 2.75 mol). The reaction is stirred at room temperature overnight. The reaction mixture is poured into water (3000 mL) and extracted with Et2O (3×1500 mL). The organic extracts are combined and washed with water (4×1000 mL), then brine, and dried over Na2SO4. The solvent is evaporated to give a light brown oil which, on standing, gives clear colorless crystals, with a little mobile liquid on top of the crystals. The liquid is decanted off and discarded to leave the product as a crystalline solid (257.3 g, 1.71 moles). 1H-NMR (400 MHz, CDCl3): δ 7.93 (t, 1H), 7.11 (d, 1H), 6.69 (d, 1H), 6.46 (d, 1H), 3.83 (s, 3H).

Workup

  1. extractionextracted with Et2O (3×1500 mL)
  2. washwashed with water (4×1000 mL)
  3. dry with materialbrine, and dried over Na2SO4
  4. customThe solvent is evaporated
  5. customto give a light brown oil which
  6. customon standing, gives clear colorless crystals
  7. customThe liquid is decanted off

Sources & evidence

ORD record
ord-59edab954b1f4b40a340b0ff84ccd008
Source dataset
uspto-grants-2014_07
Patent number
US08778946B2

Reaction notes

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