Potassium Hydroxide → 6-Bromo-1-naphthalen-1-ylmethyl-3,3-bis-pyridin-4-ylmethyl-1,3-dihydro-indol-2-one

HRID 1355669Notes

Reaction equation

HRID 1355669 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][C:7](=[O:22])[N:8]2[CH2:11][C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:15]=[CH:14][CH:13]=2)=[CH:4][CH:3]=1.[OH-].[K+].Cl.[N:26]1[CH:31]=[CH:30][C:29]([CH2:32]Cl)=[CH:28][CH:27]=1>C1COCC1>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH2:32][C:29]3[CH:30]=[CH:31][N:26]=[CH:27][CH:28]=3)([CH2:32][C:29]3[CH:30]=[CH:31][N:26]=[CH:27][CH:28]=3)[C:7](=[O:22])[N:8]2[CH2:11][C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:15]=[CH:14][CH:13]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 745704-(Chloromethyl)pyridinium chlorideHCID 185077696-Bromo-1-naphthalen-1-ylmethyl-1,3-dihydro-indol-2-one

Product 1

HCID 185077626-Bromo-1-naphthalen-1-ylmethyl-3,3-bis-pyridin-4-ylmethyl-1,3-dihydro-indol-2-oneYield 47.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

6-Bromo-1-naphthalen-1-ylmethyl-1,3-dihydro-indol-2-one (195 mg, 0.554 mmol) was dissolved in 1 ml of THF and was then added to a previously degassed solution of 3 ml of THF and 5 ml of aqueous 1 N KOH under an atmosphere of dry N2. To this solution was added 4-picolyl chloride hydrochloride (275 mg, 1.67 mmol). The reaction mixture was then stirred at ambient temperature for 2 hours after which time the reaction mixture was concentrated under vacuum to give a green oil. The oil was partitioned between DCM and saturated aqueous NaHCO3. The DCM layer was then washed with brine, dried over Na2SO4, filtered and concentrated under vacuum to give a dark oil which was chromatographed on flash silica gel eluting with a gradient from EtOAc/hexanes (50:50) to EtOAc to EtOAc/MeOH (95:5) to give 140 mg of the titled compound as a colorless oil.

Workup

  1. concentrationwas concentrated under vacuum
  2. customto give a green oil
  3. customThe oil was partitioned between DCM and saturated aqueous NaHCO3
  4. washThe DCM layer was then washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum
  8. customto give a dark oil which
  9. customwas chromatographed on flash silica gel eluting with a gradient from EtOAc/hexanes (50:50) to EtOAc to EtOAc/MeOH (95:5)

Sources & evidence

ORD record
ord-bd3a14a7105340a093c0feae8f98b08d
Source dataset
uspto-grants-2003_07
Patent number
US06586447B1

Reaction notes

Loading…