Methylamine → 5-fluoro-3-methylaminomethyl-1-naphthalen-1-ylmethyl-1H-indole-2-carboxylic acid ethyl ester

HRID 642693Notes

Reaction equation

HRID 642693 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].[CH3:29][NH2:30]>CO.CC(O)=O.O1CCCC1>[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:30][CH3:29])=[CH:12][C:11]([F:17])=[CH:10][CH:9]=2)=[O:5])[CH3:2]

Participants

6

Reactant 2

HCID 6329MethylamineHCID 866131895-fluoro-3-formyl-1-naphthalen-1-ylmethyl-1H-indole-2-carboxylic acid ethyl ester

Product 1

HCID 685785195-fluoro-3-methylaminomethyl-1-naphthalen-1-ylmethyl-1H-indole-2-carboxylic acid ethyl ester

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-fluoro-3-formyl-1-naphthalen-1-ylmethyl-1H-indole-2-carboxylic acid ethyl ester (from Example 76.1., 0.60 g) in MeOH (5.0 ml), AcOH (0.92 ml), tetrahydrofuran (2.0 ml) and methyl amine (2 M in THF, 3.2 ml) was added portion wise Na(CN)BH3 (202 mg) and stirring was continued at 22° C. for 3 h. The mixture was evaporated and the residue partitioned between 1 N aqueous HCl and dichlormethane. The pH of the aqueous layer was adjusted to 11 using NaOH, extracted with dichloromethane, dried and evaporated to give 5-fluoro-3-methylaminomethyl-1-naphthalen-1-ylmethyl-1H-indole-2-carboxylic acid ethyl ester as a colorless oil. MS: 391.3 ([M+H]+).

Workup

  1. customThe mixture was evaporated
  2. customthe residue partitioned between 1 N aqueous HCl and dichlormethane
  3. extractionextracted with dichloromethane
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-44ef5d1acc1e49ef91186bcc119b69ee
Source dataset
uspto-grants-2010_04
Patent number
US07696240B2

Reaction notes

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