Water → 5-Fluoro-6-(4-fluoro-benzylamino)-1,3-dihydro-indol-2-one

HRID 2365082Notes

Reaction equation

HRID 2365082 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][C:7](=[O:11])[NH:8]2)=[CH:4][C:3]=1[F:12].[F:13][C:14]1[CH:21]=[CH:20][C:17]([CH:18]=O)=[CH:16][CH:15]=1.[BH4-].[Na+].O>C(O)C>[F:12][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:2]=1[NH:1][CH2:18][C:17]1[CH:20]=[CH:21][C:14]([F:13])=[CH:15][CH:16]=1)[NH:8][C:7](=[O:11])[CH2:6]2

Participants

6

Reactant 4

HCID 962WaterHCID 680234-FluorobenzaldehydeHCID 4311764Sodium borohydrideHCID 101035046-Amino-5-fluoroindolin-2-one

Product 1

HCID 592500565-Fluoro-6-(4-fluoro-benzylamino)-1,3-dihydro-indol-2-oneYield 45%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred solution of d 6-amino-5-fluoro-1,3-dihydro-indol-2-one (2.26 g, 13.6 mmol) obtained from Example 6 in 40 ml of ethanol was added with 4-fluoro-benzaldehyde (1.5 ml, 13.6 mmol) at 0° C. in an ice-water bath. The resulting solution was stirred for 1 hour, added with sodium borohydride (1.08 g, 28.5 mmol) and heated to reflux overnight. The resulting mixture was added with water until a precipitate was formed. The solid was filtered and washed with water (50 ml×3). The crude was purified by silica gel column chromatography with dichloromethane and methanol (20:1) as eluents to give 5-fluoro-6-(4-fluoro-benzylamino)-1,3-dihydro-indol-2-one (1.67 g, 45%) as a white solid.

Workup

  1. temperatureheated
  2. temperatureto reflux overnight
  3. customwas formed
  4. filtrationThe solid was filtered
  5. washwashed with water (50 ml×3)
  6. customThe crude was purified by silica gel column chromatography with dichloromethane and methanol (20:1) as eluents

Sources & evidence

ORD record
ord-0c67d954f5ca4948aba40d1db5d0fac2
Source dataset
uspto-grants-2014_04
Patent number
US08697692B2

Reaction notes

Loading…