Hydrochloric Acid → 5-fluoro-3-(methoxycarbonylamino-methyl)-1-naphthalen-1-ylmethyl-1H-indole-2-carboxylic acid ethyl ester

HRID 642692Notes

Reaction equation

HRID 642692 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[CH2:15][NH2:16])=[CH:12][C:11]([F:17])=[CH:10][CH:9]=2)=[O:5])[CH3:2].Cl.Cl[C:31]([O:33][CH3:34])=[O:32]>ClCCl>[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[CH2:15][NH:16][C:31]([O:33][CH3:34])=[O:32])=[CH:12][C:11]([F:17])=[CH:10][CH:9]=2)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6586Methyl chloroformateHCID 685784813-aminomethyl-5-fluoro-1-naphthalen-1-ylmethyl-1H-indole-2-carboxylic acid ethyl ester

Product 1

HCID 685779595-fluoro-3-(methoxycarbonylamino-methyl)-1-naphthalen-1-ylmethyl-1H-indole-2-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 3-aminomethyl-5-fluoro-1-naphthalen-1-ylmethyl-1H-indole-2-carboxylic acid ethyl ester; salt with hydrogen chloride (from Example 76.3., 0.2 mmole) in dichloromethane (2.0 ml) was added at 22° C. methyl chloroformate (0.22 mmole) and stirring was continued at 22° C. for 16 h. The mixture was washed with 1 N aqueous HCl, the organic layer was dried, evaporated and the residue was chromatographed on silica using n-heptane/AcOEt to give 5-fluoro-3-(methoxycarbonylamino-methyl)-1-naphthalen-1-ylmethyl-1H-indole-2-carboxylic acid ethyl ester as a colorless solid. MS: 435.4 ([M+H]+).

Workup

  1. washThe mixture was washed with 1 N aqueous HCl
  2. customthe organic layer was dried
  3. customevaporated
  4. customthe residue was chromatographed on silica

Sources & evidence

ORD record
ord-5f754690070d43948cfeaa5e2e816308
Source dataset
uspto-grants-2010_04
Patent number
US07696240B2

Reaction notes

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