Hydrochloric Acid → 4-[(E)-2-ethoxyvinyl]-1-[(4-fluorophenyl)methyl]pyrrolo[2,3-c]pyridine-5-carbohydroxamic acid

HRID 640699Notes

Reaction equation

HRID 640699 reaction equation
[CH2:1]([O:3]/[CH:4]=[CH:5]/[C:6]1[C:11]([C:12](OC)=[O:13])=[N:10][CH:9]=[C:8]2[N:16]([CH2:19][C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=3)[CH:17]=[CH:18][C:7]=12)[CH3:2].[NH2:27][OH:28].[OH-].[Na+].Cl>CO>[CH2:1]([O:3]/[CH:4]=[CH:5]/[C:6]1[C:11]([C:12]([NH:27][OH:28])=[O:13])=[N:10][CH:9]=[C:8]2[N:16]([CH2:19][C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=3)[CH:17]=[CH:18][C:7]=12)[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 787HydroxylamineHCID 14798Sodium HydroxideHCID 686652681h-Pyrrolo[2,3-c]pyridine-5-carboxylic acid,4-[(1e)-2-ethoxyethenyl]-1-[(4-fluorophenyl)methyl]-,methyl ester

Product 1

HCID 159570544-[(E)-2-ethoxyvinyl]-1-[(4-fluorophenyl)methyl]pyrrolo[2,3-c]pyridine-5-carbohydroxamic acidYield 100.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To methyl 4-[(E)-2-ethoxyvinyl]-1-(4-fluorobenzyl)-1H-pyrrolo[2,3-c]pyridine-5-carboxylate (0.1 g, 0.28 mmol) in methanol (10 mL) were added hydroxylamine (1 mL, 50% in water, 15.2 mmol) and sodium hydroxide (63.8 mg, 1.59 mmol). The mixture was stirred at room temperature for 2 h, and 4N hydrochloric acid (0.5 mL, 1.9 mmol) was added. The mixture was concentrated to provide 100 mg of the title compound that was used without further purification in the next step. 1H NMR (DMSO-d6) δ ppm 11.76 (d, 1H, J=1.9 Hz), 8.88 (d, 1H, J=1.9 Hz), 8.60 (s, 1H), 7.83 (d, 1H, J=3.0 Hz), 7.31 (t, 2H, J=8.9 Hz), 7.22 (d, 1H, J=13.2 Hz), 7.05 (t, 2H, J=8.9 Hz), 6.82 (d, 1 H, J=3.0 Hz), 6.66 (d, 1 H, J=13.2 Hz), 5.54 (s, 2H), 3.96 (q, 2H, J=7.0 Hz), 1.28 (t, 3H, J=7.0 Hz). LCMS (APCl, M+H+): 356.

Workup

  1. concentrationThe mixture was concentrated

Sources & evidence

ORD record
ord-a1cd88a7ca054135bb84867581177f98
Source dataset
uspto-grants-2010_04
Patent number
US07692014B2

Reaction notes

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