Sodium Acetate → 3-aminomethyl-5-fluoro-1-naphthalen-1-ylmethyl-1H-indole-2-carboxylic acid ethyl ester

HRID 642690Notes

Reaction equation

HRID 642690 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH2:19][C:20]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[CH:23]=[CH:22][CH:21]=2)[C:8]2[C:13]([C:14]=1[CH:15]=[N:16]O)=[CH:12][C:11]([F:18])=[CH:10][CH:9]=2)=[O:5])[CH3:2].C([O-])(=O)C.[Na+]>CC(O)=O.[Zn]>[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH2:19][C:20]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[CH:23]=[CH:22][CH:21]=2)[C:8]2[C:13]([C:14]=1[CH2:15][NH2:16])=[CH:12][C:11]([F:18])=[CH:10][CH:9]=2)=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 517045Sodium AcetateHCID 866131905-fluoro-3-(hydroxyimino-methyl)-1-naphthalen-1-ylmethyl-1H-indole-2-carboxylic acid ethyl ester

Product 1

HCID 685784813-aminomethyl-5-fluoro-1-naphthalen-1-ylmethyl-1H-indole-2-carboxylic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of 5-fluoro-3-(hydroxyimino-methyl)-1-naphthalen-1-ylmethyl-1H-indole-2-carboxylic acid ethyl ester (1.17 g) in AcOH (75 ml) was added at 22° C. sodium acetate (4.9 g) followed by portion wise addition of zinc dust (0.78 g) and stirring was continued at 22° C. for 3 h. The mixture was evaporated and the residue partitioned between ice-cold aqueous 2 N NaOH and t-butylmethyl ether. The aqueous layer was extracted several times; the combined organic layers were dried and evaporated. The residue was dissolved in EtOH saturated with HCl (10 ml), the solution was stirred at 22° C. for 16 h and evaporated again. The residue was suspended in t-butylmethyl ether and the suspension was filtered to give 3-aminomethyl-5-fluoro-1-naphthalen-1-ylmethyl-1H-indole-2-carboxylic acid ethyl ester; salt with hydrogen chloride as a yellow solid. MS: 377.3 ([M+H]+).

Workup

  1. customThe mixture was evaporated
  2. customthe residue partitioned between ice-cold aqueous 2 N NaOH and t-butylmethyl ether
  3. extractionThe aqueous layer was extracted several times
  4. customthe combined organic layers were dried
  5. customevaporated
  6. dissolutionThe residue was dissolved in EtOH saturated with HCl (10 ml)
  7. stirringthe solution was stirred at 22° C. for 16 h
  8. customevaporated again
  9. filtrationthe suspension was filtered

Sources & evidence

ORD record
ord-1b6918c3f0a04fa98ec2de80e7fd6526
Source dataset
uspto-grants-2010_04
Patent number
US07696240B2

Reaction notes

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