Sodium Bicarbonate → HCID 9951446, compound

HRID 2209972Notes

Reaction equation

HRID 2209972 reaction equation
Br[CH2:2][CH2:3][CH:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][C:6](=[O:14])[CH2:5]1.[NH:15]1[CH2:20][CH2:19][CH:18]([C:21]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[NH:23][CH:22]=2)[CH2:17][CH2:16]1.C(=O)([O-])O.[Na+]>CN(C)C=O>[NH:23]1[C:24]2[C:29](=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:21]([CH:18]2[CH2:19][CH2:20][N:15]([CH2:2][CH2:3][CH:4]3[C:13]4[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=4)[NH:7][C:6](=[O:14])[CH2:5]3)[CH2:16][CH2:17]2)=[CH:22]1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 7022353-(4-Piperidinyl)-1H-indoleHCID 193797004-(2-bromoethyl)-3,4-dihydro-2(1H)-quinolinone

Product 1

HCID 9951446HCID 9951446, compoundYield 73.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 4-(2-bromoethyl)-3,4-dihydro-2(1H)-quinolinone (II'-1) (500 mg, 1.97 mmol),3-(4-piperidinyl)-1H-indole (394.5 mg, 1.97 mmol) and sodium hydrogencarbonate (248.7 mg, 2.96 mmol) in dry dimethylformamide (5 ml) was allowed to react at 90 ° C. for 4 hours. Ice-water (50 ml) was poured into the reaction mixture and then the separated solid was filtered by aspiration. The residue was washed with water and dissolved in chloroform (50 ml). The solution was dried (anhydrous magnesium sulfate) and the solvent was distilled off. The residue was dissolved in developing solvent (chloroform: methanol=85:15) and purified by silica gel column chromatography (chloroform: methanol=85:15). After removing the first eluted impurity , a colorless solution was collected and the solvent distilled off to give the desired product (IV-1) (540 mg) as a pale yellow solid (yield 73.4%, mp 115°-117 ° C. (methanol/tetrahydrofuran/water).

Workup

  1. customto react at 90 ° C. for 4 hours
  2. filtrationthe separated solid was filtered by aspiration
  3. washThe residue was washed with water
  4. dissolutiondissolved in chloroform (50 ml)
  5. dry with materialThe solution was dried (anhydrous magnesium sulfate)
  6. distillationthe solvent was distilled off
  7. dissolutionThe residue was dissolved
  8. custompurified by silica gel column chromatography (chloroform: methanol=85:15)
  9. customAfter removing the first eluted impurity
  10. customa colorless solution was collected
  11. distillationthe solvent distilled off

Sources & evidence

ORD record
ord-bf1fee319ed445baa3439e228a57f8eb
Source dataset
uspto-grants-1995_10
Patent number
US05457099

Reaction notes

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