Pyridine → 5-fluoro-3-(hydroxyimino-methyl)-1-naphthalen-1-ylmethyl-1H-indole-2-carboxylic acid ethyl ester

HRID 642689Notes

Reaction equation

HRID 642689 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH2:18][C:19]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH:22]=[CH:21][CH:20]=2)[C:8]2[C:13]([C:14]=1[CH:15]=O)=[CH:12][C:11]([F:17])=[CH:10][CH:9]=2)=[O:5])[CH3:2].N1C=CC=CC=1.Cl.[NH2:36][OH:37]>CCO>[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH2:18][C:19]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH:22]=[CH:21][CH:20]=2)[C:8]2[C:13]([C:14]=1[CH:15]=[N:36][OH:37])=[CH:12][C:11]([F:17])=[CH:10][CH:9]=2)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 443297Hydroxyamine hydrochlorideHCID 866131895-fluoro-3-formyl-1-naphthalen-1-ylmethyl-1H-indole-2-carboxylic acid ethyl ester

Product 1

HCID 866131905-fluoro-3-(hydroxyimino-methyl)-1-naphthalen-1-ylmethyl-1H-indole-2-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 5-fluoro-3-formyl-1-naphthalen-1-ylmethyl-1H-indole-2-carboxylic acid ethyl ester (1.16 g) in EtOH (35 ml) was added at 22° C. pyridine (8.0 ml) and hydroxylamine hydrochloride (0.54 g) and the mixture was heated to reflux temperature for 2 h. The mixture was evaporated and the residue partitioned between 1 N HCl and t-butylmethyl ether. The organic layer was dried and evaporated to give 5-fluoro-3-(hydroxyimino-methyl)-1-naphthalen-1-ylmethyl-1H-indole-2-carboxylic acid ethyl ester as a colorless foam. MS: 391.1 ([M+H]+).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux temperature for 2 h
  3. customThe mixture was evaporated
  4. customthe residue partitioned between 1 N HCl and t-butylmethyl ether
  5. customThe organic layer was dried
  6. customevaporated

Sources & evidence

ORD record
ord-5d337144339542098d9eda8974075333
Source dataset
uspto-grants-2010_04
Patent number
US07696240B2

Reaction notes

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