Sodium hydride → HCID 17959426, compound

HRID 2245280Notes

Reaction equation

HRID 2245280 reaction equation
[H-].[Na+].[NH2:3][C:4]1[C:9]([Cl:10])=[CH:8][N:7]=[CH:6][C:5]=1[Cl:11].[CH3:12][O:13][C:14]1[CH:15]=[C:16]([CH:32]=[CH:33][CH:34]=1)[CH2:17][N:18]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][N:25]=2)[C:20]([C:27](=[O:31])[C:28](Cl)=[O:29])=[CH:19]1>C1COCC1>[Cl:11][C:5]1[CH:6]=[N:7][CH:8]=[C:9]([Cl:10])[C:4]=1[NH:3][C:28](=[O:29])[C:27]([C:20]1[C:21]2[C:26](=[N:25][CH:24]=[CH:23][CH:22]=2)[N:18]([CH2:17][C:16]2[CH:32]=[CH:33][CH:34]=[C:14]([O:13][CH3:12])[CH:15]=2)[CH:19]=1)=[O:31]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 898884-Amino-3,5-dichloropyridineHCID 179594641h-Pyrrolo[2,3-b]pyridine-3-acetyl chloride,1-[(3-methoxyphenyl)methyl]-a-oxo-

Product 1

HCID 17959426HCID 17959426, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of 2 g of sodium hydride in 20 mL of THF, 2.4 g of 4-amino-3,5-dichloropyridine (15 mmoles) in 30 mL of THF are added dropwise at −5° C. The mixture is then kept for one hour at 20° C. with stirring. Subsequently, the previously prepared suspension of 1-(3-methoxybenzyl)-7-azaindole-3-yl-glyoxylic acid chloride is added dropwise at about 0° C. Finally, the reaction mixture is refluxed for 4 hours, after which the solvent is removed under vacuum. The residue is stirred with 50 mL of ethyl acetate and 50 mL of water. The phases are separated and the organic phase is washed with water. The solvent is distilled off under vacuum and the residue recrystallized from isopropanol.

Workup

  1. additionare added dropwise at −5° C
  2. additionis added dropwise at about 0° C
  3. temperatureFinally, the reaction mixture is refluxed for 4 hours
  4. customafter which the solvent is removed under vacuum
  5. stirringThe residue is stirred with 50 mL of ethyl acetate and 50 mL of water
  6. customThe phases are separated
  7. washthe organic phase is washed with water
  8. distillationThe solvent is distilled off under vacuum
  9. customthe residue recrystallized from isopropanol

Sources & evidence

ORD record
ord-06a7a65c2004439d82f28d9eb92fa990
Source dataset
uspto-grants-2010_03
Patent number
US07683074B2

Reaction notes

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