5-[5-(Allyl-methyl-amino)-pent-1-ynyl]-6-fluoro-2,3-dihydro-indole-1-carboxylic acid 4-chloro-phenyl ester → 6-Fluoro-5-[5-(methyl-propyl-amino)-pentyl]-2,3-dihydro-indole-1-carboxylic acid phenyl ester

HRID 49522Notes

Reaction equation

HRID 49522 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]([N:11]2[C:19]3[C:14](=[CH:15][C:16]([C:21]#[C:22][CH2:23][CH2:24][CH2:25][N:26]([CH2:28][CH:29]=[CH2:30])[CH3:27])=[C:17]([F:20])[CH:18]=3)[CH2:13][CH2:12]2)=[O:10])=[CH:4][CH:3]=1>CC(O)=O.[Pd]>[C:5]1([O:8][C:9]([N:11]2[C:19]3[C:14](=[CH:15][C:16]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][N:26]([CH3:27])[CH2:28][CH2:29][CH3:30])=[C:17]([F:20])[CH:18]=3)[CH2:13][CH2:12]2)=[O:10])[CH:6]=[CH:7][CH:2]=[CH:3][CH:4]=1

Participants

4

Reactant 1

HCID 101373155-[5-(Allyl-methyl-amino)-pent-1-ynyl]-6-fluoro-2,3-dihydro-indole-1-carboxylic acid 4-chloro-phenyl ester

Product 1

HCID 101355116-Fluoro-5-[5-(methyl-propyl-amino)-pentyl]-2,3-dihydro-indole-1-carboxylic acid phenyl esterYield 64%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

Hydrogenolysis at atmospheric pressure of 5 mg (0.013 mmol) 5-[5-(Allyl-methyl-amino)-pent-1-ynyl]-6-fluoro-2,3-dihydro-indole-1-carboxylic acid 4-chloro-phenyl ester in 0.5 ml AcOH in the presence of 5 mg 10% Pd/C during 12 hrs, followed by filtration, evaporation of the AcOH, distribution of the residue between Et2O and 0.5 M NaOH, drying of the organic layer with Na2SO4, evaporation of the solvent and chromatograpy on silica gel with EtOAc/MeOH/NEt3 10:1:0.1 gave 3 mg (64%) of 6-Fluoro-5-[5-(methyl-propyl-amino)-pentyl]-2,3-dihydro-indole-1-carboxylic acid phenyl ester as a yellow oil, MS: 399 (MH+)

Workup

  1. filtrationfollowed by filtration, evaporation of the AcOH, distribution of the residue between Et2O and 0.5 M NaOH
  2. dry with materialdrying of the organic layer with Na2SO4, evaporation of the solvent and chromatograpy on silica gel with EtOAc/MeOH/NEt3 10:1:0.1

Sources & evidence

ORD record
ord-92a2c440c5ef4329b2f91378cbcc5743
Source dataset
uspto-grants-2004_03
Patent number
US06706751B2

Reaction notes

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