Potassium Hydroxide → HCID 18507756, compound

HRID 1355667Notes

Reaction equation

HRID 1355667 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6](=[CH:25][C:26]3[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=3)[C:7](=[O:24])[N:8]2[CH2:11][C:12]2[CH:17]=[CH:16][C:15]([S:18]([N:21]([CH3:23])[CH3:22])(=[O:20])=[O:19])=[CH:14][CH:13]=2)=[CH:4][CH:3]=1.[BH4-].[Na+].[OH-].[K+].Cl.[N:37]1[CH:42]=[CH:41][C:40]([CH2:43]Cl)=[CH:39][CH:38]=1>CO.C1COCC1>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH2:43][C:40]3[CH:41]=[CH:42][N:37]=[CH:38][CH:39]=3)([CH2:25][C:26]3[CH:27]=[CH:28][N:29]=[CH:30][CH:31]=3)[C:7](=[O:24])[N:8]2[CH2:11][C:12]2[CH:13]=[CH:14][C:15]([S:18]([N:21]([CH3:23])[CH3:22])(=[O:19])=[O:20])=[CH:16][CH:17]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 14797Potassium HydroxideHCID 745704-(Chloromethyl)pyridinium chlorideHCID 4311764Sodium borohydrideHCID 70033600HCID 70033600, compound

Product 1

HCID 18507756HCID 18507756, compoundYield 37.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

4-(6-Bromo-2-oxo-3-pyridin-4-ylmethylene-2,3-dihydro-indol-1-ylmethyl)-N,N-dimethyl-benzenesulfonamide (1.45 g, 2.92 mmol) was dissolved in a previously degassed solution of 50 ml of methanol and 50 ml of THF under an atmosphere of dry N2. To this solution was added sodium borohydride (177 mg, 4.67 mmol). The reaction was stirred at ambient temperature for 1.5 hours after which time 11.7 ml of aqueous 1.0 N potassium hydroxide (KOH) was added followed by the addition of 4-picolyl chloride hydrochloride (520 mg, 3.08 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 dark oil. The dark 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 (60:40) to EtOAc/Hexanes (80:20) to give 650 mg of the titled compound as a pink solid.

Workup

  1. additionwas added
  2. concentrationwas concentrated under vacuum
  3. customto give a dark oil
  4. customThe dark oil was partitioned between DCM and saturated aqueous NaHCO3
  5. washThe DCM layer was then washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum
  9. customto give a dark oil which
  10. customwas chromatographed on flash silica gel eluting with a gradient from EtOAc/hexanes (60:40) to EtOAc/Hexanes (80:20)

Sources & evidence

ORD record
ord-80bf4704de49406ab823b64e3c5ca983
Source dataset
uspto-grants-2003_07
Patent number
US06586447B1

Reaction notes

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