Sodium Hydroxide → Allyl-{4-[1-(4-chloro-phenyl)-6-fluoro-2,3-dihydro-1H-indole-5-yloxy]-butyl}-methyl-amine

HRID 1633711Notes

Reaction equation

HRID 1633711 reaction equation
[CH2:1]([N:4]([CH2:6][CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][C:19]=1[F:20])[N:16]([C:21]1[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=1)[CH:15]=[CH:14]2)[CH3:5])[CH:2]=[CH2:3].[OH-].[Na+]>CC(O)=O.C(O)(C(F)(F)F)=O>[CH2:1]([N:4]([CH2:6][CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][C:19]=1[F:20])[N:16]([C:21]1[CH:22]=[CH:23][C:24]([Cl:27])=[CH:25][CH:26]=1)[CH2:15][CH2:14]2)[CH3:5])[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 18679530Allyl-{4-[1-(4-chloro-phenyl)-6-fluoro-1H-indol-5-yloxy]-butyl}-methyl-amine

Product 1

HCID 18679449Allyl-{4-[1-(4-chloro-phenyl)-6-fluoro-2,3-dihydro-1H-indole-5-yloxy]-butyl}-methyl-amineYield 80%

Reagents, catalysts & solvents 1

HCID 23437676Trifluoroacetic acid acetateSolvent

Procedure

A solution of 25 mg (0.67 mol) Allyl-{4-[1-(4-chloro-phenyl)-6-fluoro-1H-indol-5-yloxy]-butyl}-methyl-amine in 1 ml AcOH/TFA (1:1) was treated at 0° C. with 70 mg (1.11 mmol) NaBCNH3 and stirred at room temperature for 8 hours. The mixture was poured into icy 2M NaOH and extracted three times with Et2O. Evaporation of the solvent, drying with MgSO4 and column chromatography on silica gel with CH2Cl2/MeOH/NEt3 10:1:0.1 gave 20 mg (80%) Allyl-{4-[1-(4-chloro-phenyl)-6-fluoro-2,3-dihydro-1H-indole-5-yloxy]-butyl}-methyl-amine, MS: 389 (MH+).

Workup

  1. extractionextracted three times with Et2O
  2. customEvaporation of the solvent
  3. dry with materialdrying with MgSO4 and column chromatography on silica gel with CH2Cl2/MeOH/NEt3 10:1:0.1

Sources & evidence

ORD record
ord-29a3f67555ee4fce952f2c0d56137ede
Source dataset
uspto-grants-2003_01
Patent number
US06503907B2

Reaction notes

Loading…