Oxalyl chloride → 1h-Pyrrolo[2,3-b]pyridine-3-acetyl chloride,1-[(3-methoxyphenyl)methyl]-a-oxo-

HRID 1375425Notes

Reaction equation

HRID 1375425 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:16]=[CH:17][CH:18]=1)[CH2:6][N:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][N:14]=2)[CH:9]=[CH:8]1.[C:19](Cl)(=[O:23])[C:20]([Cl:22])=[O:21]>COC(C)(C)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:16]=[CH:17][CH:18]=1)[CH2:6][N:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][N:14]=2)[C:9]([C:19](=[O:23])[C:20]([Cl:22])=[O:21])=[CH:8]1

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 179593931h-Pyrrolo[2,3-b]pyridine,1-[(3-methoxyphenyl)methyl]-

Product 1

HCID 179594641h-Pyrrolo[2,3-b]pyridine-3-acetyl chloride,1-[(3-methoxyphenyl)methyl]-a-oxo-

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent2×

Procedure

1-(3-Methoxybenzyl)-7-azaindole (3.57 g, 15 mmoles) is dissolved in 50 mL of t-butyl methyl ether. A solution of 1.54 mL of oxalyl chloride (18 mmoles) in 10 mL of t-butyl methyl ether is added dropwise at 0° C. with stirring. Subsequently, the mixture is refluxed for 2 hours, after which the solvent is distilled off under vacuum. The resulting 1-(3-methoxybenzyl)-7-azaindole-3-yl-glyoxylic acid chloride is obtained as a solid residue, which is suspended in 50 mL of tetrahydrofuran (THF).

Workup

  1. temperatureSubsequently, the mixture is refluxed for 2 hours
  2. distillationafter which the solvent is distilled off under vacuum

Sources & evidence

ORD record
ord-09c7081200c94ed79bcc911818276502
Source dataset
uspto-grants-2007_01
Patent number
US07169787B2

Reaction notes

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