Sodium Iodide → HCID 68896791, compound

HRID 1437157Notes

Reaction equation

HRID 1437157 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][N:5]1[C:9]2=[N:10][CH:11]=[CH:12][CH:13]=[C:8]2[C:7]([CH:14]2[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]2)=[CH:6]1.[CH3:20][O:21][C:22](=[O:31])[C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([CH2:29]Br)[CH:24]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CCCC(=O)C.O>[CH3:20][O:21][C:22](=[O:31])[C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([CH2:29][N:17]2[CH2:18][CH2:19][CH:14]([C:7]3[C:8]4[C:9](=[N:10][CH:11]=[CH:12][CH:13]=4)[N:5]([CH2:4][CH2:3][O:2][CH3:1])[CH:6]=3)[CH2:15][CH2:16]2)[CH:24]=1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 517981Methyl 3-(bromomethyl)benzoateHCID 179729681-(2-Methoxyethyl)-3-(4-piperidinyl)-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 68896791HCID 68896791, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 78952-PentanoneSolvent

Procedure

0.42 g (1.62 mmol) of 1-(2-methoxyethyl)-3-piperidin-4-yl-1H-pyrrolo[2,3-b]pyridine and 0.45 g (1.94 mmol) of 3-bromomethylbenzoic acid methyl ester were solved in 9 ml of 4-methyl-2-butanone and 0.67 g (4.86 mmol) of potassium carbonate and 0.02 g (0.16 mmol) of sodium iodide were added. The mixture was refluxed for 18 hours and, after cooling, water was added, the organic layer separated and washed with water and brine. The solvent was distilled off. The crude material weighed 0.67 g and was used in the following step without further purification.

Workup

  1. temperatureThe mixture was refluxed for 18 hours
  2. temperatureafter cooling
  3. customthe organic layer separated
  4. washwashed with water and brine
  5. distillationThe solvent was distilled off
  6. customwas used in the following step without further purification

Sources & evidence

ORD record
ord-e23d88f43dec47969ad2636fed30309e
Source dataset
uspto-grants-2009_11
Patent number
US07622480B2

Reaction notes

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