Methyl iodide → HCID 69202452, compound

HRID 2218499Notes

Reaction equation

HRID 2218499 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:8]([C:11]2[C:19]3[C:14](=[N:15][CH:16]=[CH:17][CH:18]=3)[N:13]([CH2:20][CH:21]3[CH2:25][CH2:24][CH2:23][NH:22]3)[CH:12]=2)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.I[CH3:27]>CN(C=O)C.O>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([S:8]([C:11]2[C:19]3[C:14](=[N:15][CH:16]=[CH:17][CH:18]=3)[N:13]([CH2:20][CH:21]3[CH2:25][CH2:24][CH2:23][N:22]3[CH3:27])[CH:12]=2)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 6328Methyl iodideHCID 9976793HCID 9976793, compound

Product 1

HCID 69202452HCID 69202452, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A suspension of 3-(3-chlorophenylsulfonyl)-1-(pyrrolidin-2-ylmethyl)-1H-pyrrolo[2,3-b]pyridine (0.09 g, 0.24 mmol) in DMF under a nitrogen atmosphere at room temperature is treated with iodomethane (0.021 mL, 0.34 mmol), stirred at room temperature for 18 h, diluted with water and extracted with ethyl acetate. The extracts are combined, washed sequentially with water and brine and concentrated in vacuo. The resultant residue is purified by flash chromatography (5% methanol in CH2Cl2 as eluent) to afford the free amine of the title product. The amine is dissolved in Et2O, treated with an etheral solution of anhydrous HCl, stirred and concentrated in vacuo'to afford the title compound as a solid, 30 mg, mp 149-150° C., identified by HNMR and mass spectral analyses.

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed sequentially with water and brine
  3. concentrationconcentrated in vacuo
  4. customThe resultant residue is purified by flash chromatography (5% methanol in CH2Cl2 as eluent)

Sources & evidence

ORD record
ord-717e9b47123c4332a0e65e55e6354f07
Source dataset
uspto-grants-2008_08
Patent number
US07411064B2

Reaction notes

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