Methyl iodide → 5-(1,3-Dioxolan-2-yl)-1-methyl-1H-pyrrolo[2,3-c]pyridine

HRID 1072999Notes

Reaction equation

HRID 1072999 reaction equation
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[CH:7]=[C:8]2[CH:14]=[CH:13][NH:12][C:9]2=[CH:10][N:11]=1.[H-].[Na+].[CH3:17]I>C1COCC1>[O:3]1[CH2:4][CH2:5][O:1][CH:2]1[C:6]1[CH:7]=[C:8]2[CH:14]=[CH:13][N:12]([CH3:17])[C:9]2=[CH:10][N:11]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 14644282HCID 14644282, compound

Product 1

HCID 220470575-(1,3-Dioxolan-2-yl)-1-methyl-1H-pyrrolo[2,3-c]pyridineYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-(1,3-Dioxolan-2-yl)-1H-pyrrolo[2,3-c]pyridine (C173) (1.05 g, 5.52 mmol) is dissolved in 20 mL THF in a dried flask under N2. 60% Sodium hydride (243 mg, 6.07 mmol) is added, the reaction is stirred 30 min, methyl iodide (360 μL, 5.8 mmol) is added, and the reaction is stirred overnight at rt. The reaction is concentrated in vacuo and the residue is partitioned between 10 mL saturated NaCl and CH2Cl2 (4×10 mL). The combined organic layer is dried over anhydrous K2CO3 and is concentrated in vacuo to a tan paste. The crude material is chromatographed over 50 g silica gel (230-400 mesh) eluting with 5% MeOH/CH2Cl2. The appropriate fractions are combined and concentrated to afford 5-(1,3-dioxolan-2-yl)-1-methyl-1H-pyrrolo[2,3-c]pyridine (C175) (86% yield). HRMS (FAB) calculated for C11H12N2O2+H: 205.0977, found 205.0983.

Workup

  1. stirringthe reaction is stirred overnight at rt
  2. concentrationThe reaction is concentrated in vacuo
  3. customthe residue is partitioned between 10 mL saturated NaCl and CH2Cl2 (4×10 mL)
  4. dry with materialThe combined organic layer is dried over anhydrous K2CO3
  5. concentrationis concentrated in vacuo to a tan paste
  6. customThe crude material is chromatographed over 50 g silica gel (230-400 mesh)
  7. washeluting with 5% MeOH/CH2Cl2
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-c41c61878944483d92821bbbb54f7279
Source dataset
uspto-grants-2005_06
Patent number
US06911543B2

Reaction notes

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