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Sodium hydride → HCID 17959426, compound

HRID 28455
Notes
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Reaction equation

HRID 28455 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 ispropanol.

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 ispropanol

Sources & evidence

ORD record
ord-5133f27b413943509b07aa12648a22b3
Source dataset
uspto-grants-2008_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07419987B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes