Benzaldehyde → 6-[3-(benzylamino)benzoyl]-1,3-dihydro-2H-indol-2-one

HRID 2352986Notes

Reaction equation

HRID 2352986 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][CH:19]=1)[C:5]([C:7]1[CH:15]=[C:14]2[C:10]([CH2:11][C:12](=[O:16])[NH:13]2)=[CH:9][CH:8]=1)=[O:6].[CH:20](=O)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C([BH3-])#N.[Na+].C1COCC1>O.C(O)(=O)C>[CH2:20]([NH:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][CH:19]=1)[C:5]([C:7]1[CH:15]=[C:14]2[C:10]([CH2:11][C:12](=[O:16])[NH:13]2)=[CH:9][CH:8]=1)=[O:6])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

7

Reactant 4

HCID 240BenzaldehydeHCID 8028TetrahydrofuranHCID 5003444Sodium cyanoborohydrideHCID 592564786-(3-Amino-benzoyl)-1,3-dihydro-indol-2-one

Product 1

HCID 687015966-[3-(benzylamino)benzoyl]-1,3-dihydro-2H-indol-2-oneYield 26%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A dry round bottom flask was charged with 6-(3-Amino-benzoyl)-1,3-dihydro-indol-2-one (as prepared in Example 40, 0.100 g, 0.397 mmol), benzaldehyde (0.042 g, 0.397 mmol) and acetic acid (0.1 mL). The mixture was allowed to stir for 5 hours at room temperature. A 1M solution of sodium cyanoborohydride in THF (1.19 mL, 1.19 mmol) was then added, and the mixture was allowed to stir for 45 minutes. Subsequently the reaction mixture was poured into H2O (˜30 mL) and allowed to stir for 15 minutes. The suspension was filtered and the filtrate was extracted with EtOAc (3ט10 mL). The organics were dried over anhydrous Na2SO4, filtered and concentrated in vacuo to afford a brown oil. The brown oil was then chromatographed over silica (97/3, chloroform/methanol w/0.5% NEt3) to afford 6-[3-(benzylamino)benzoyl]-1,3-dihydro-2H-indol-2-one in 26% yield (0.035 g, 0.103 mmol).

Workup

  1. stirringto stir for 45 minutes
  2. stirringto stir for 15 minutes
  3. filtrationThe suspension was filtered
  4. extractionthe filtrate was extracted with EtOAc (3ט10 mL)
  5. dry with materialThe organics were dried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto afford a brown oil
  9. customThe brown oil was then chromatographed over silica (97/3, chloroform/methanol w/0.5% NEt3)

Sources & evidence

ORD record
ord-0eacee2d04574227a860e05076c317b6
Source dataset
uspto-grants-2010_07
Patent number
US07749530B2

Reaction notes

Loading…