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

HRID 2377082Notes

Reaction equation

HRID 2377082 reaction equation
[CH2:1]([O:3]/[CH:4]=[CH:5]/[C:6]1[C:11]([C:12]([O:14]CC)=O)=[N:10][CH:9]=[C:8]2[N:17]([CH2:20][C:21]3[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=3)[CH:18]=[CH:19][C:7]=12)[CH3:2].[NH2:28][OH:29].[OH-].[Na+].Cl>CO>[CH2:1]([O:3]/[CH:4]=[CH:5]/[C:6]1[C:11]([C:12]([NH:28][OH:29])=[O:14])=[N:10][CH:9]=[C:8]2[N:17]([CH2:20][C:21]3[CH:22]=[CH:23][C:24]([F:27])=[CH:25][CH:26]=3)[CH:18]=[CH:19][C:7]=12)[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 787HydroxylamineHCID 14798Sodium HydroxideHCID 686655661h-Pyrrolo[2,3-c]pyridine-5-carboxylic acid,4-[(1e)-2-ethoxyethenyl]-1-[(4-fluorophenyl)methyl]-,ethyl ester

Product 1

HCID 159570544-[(E)-2-ethoxyvinyl]-1-[(4-fluorophenyl)methyl]pyrrolo[2,3-c]pyridine-5-carbohydroxamic acidYield 62.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To ethyl 4-[(E)-2-ethoxyvinyl]-1-(4-fluorobenzyl)-1H-pyrrolo[2,3-c]pyridine-5-carboxylate (0.2 g, 0.54 mmol) in methanol (5 mL) were added hydroxylamine (1 mL, 50% in water, 15.2 mmol) and sodium hydroxide (0.0763 g, 1.9 mmol). The mixture was stirred at room temperature for 5 h, neutralized with 4N aq. HCl solution (0.48 mL, 1.9 mmol), and extracted with ethyl acetate. The organic extract was concentrated and recrystallized from ethyl acetate/ethyl ether/hexane to give the title compound (0.12 g, 62% yield). 1H NMR (DMSO-d6) 6; 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, 1H, J=3.0 Hz), 6.66 (d, 1H, 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 (APCI, M+H+): 356.1. Anal. (C19H18FN3O3) C, H, N. HPLC: 95% purity.

Workup

  1. extractionextracted with ethyl acetate
  2. extractionThe organic extract
  3. concentrationwas concentrated
  4. customrecrystallized from ethyl acetate/ethyl ether/hexane

Sources & evidence

ORD record
ord-8a3eb828231a4b02929bb82a90647957
Source dataset
uspto-grants-2008_12
Patent number
US07468375B2

Reaction notes

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