Sodium Bicarbonate → Swr 00151

HRID 2209966Notes

Reaction equation

HRID 2209966 reaction equation
Br[CH2:2][CH2:3][C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][C:6](=[O:14])[CH: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][C:4]3[C:13]4[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=4)[NH:7][C:6](=[O:14])[CH:5]=3)[CH2:16][CH2:17]2)=[CH:22]1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 7022353-(4-Piperidinyl)-1H-indoleHCID 134715054-(2-Bromoethyl)quinolin-2(1H)-one

Product 1

HCID 3073949Swr 00151Yield 45.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 4-(2-bromethyl)-2-(1H)-quinolinone (II-2) (500 mg, 1.98 mmol), 3-(4-piperidinyl)-1H-indole (396.5 mg, 1.98 mmol) and sodium hydrogencarbonate (249.5 mg, 2.97 mmol) in dry dimethylformamide (5 ml) was react at 80 ° C. for 5 hours. The reaction mixture was poured into ice-water and the separated solid was filtered by aspiration. The residue was washed with water and recrystallized from methanol/tetrahydrofuran/water to give the desired product (336 mg) (III-2) as pale yellow crystals (mp 259°-260 ° C. (methanol/tetrahydrofuran/water)). Yield 45.7%.

Workup

  1. customwas react at 80 ° C. for 5 hours
  2. filtrationthe separated solid was filtered by aspiration
  3. washThe residue was washed with water
  4. customrecrystallized from methanol/tetrahydrofuran/water

Sources & evidence

ORD record
ord-03c5fea7f5b84241982399bdf9e3a934
Source dataset
uspto-grants-1995_10
Patent number
US05457099

Reaction notes

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