Sodium hydride → 2-[4-[2-(1-Pyrrolidinyl)ethoxy]phenyl]-benzo[b]thiophen-3-yl 4-[2-(2-Oxopyrrolidin-1-yl)ethoxy]-phenyl Ketone

HRID 1700773Notes

Reaction equation

HRID 1700773 reaction equation
[H-].[Na+].[OH:3][CH2:4][CH2:5][N:6]1[CH2:10][CH2:9][CH2:8][C:7]1=[O:11].[N:12]1([CH2:17][CH2:18][O:19][C:20]2[CH:25]=[CH:24][C:23]([C:26]3[S:30][C:29]4[CH:31]=[CH:32][CH:33]=[CH:34][C:28]=4[C:27]=3[C:35]([C:37]3[CH:42]=[CH:41][C:40](F)=[CH:39][CH:38]=3)=[O:36])=[CH:22][CH:21]=2)[CH2:16][CH2:15][CH2:14][CH2:13]1>CN(C=O)C.[Cl-].[Na+].O>[O:11]=[C:7]1[CH2:8][CH2:9][CH2:10][N:6]1[CH2:5][CH2:4][O:3][C:40]1[CH:41]=[CH:42][C:37]([C:35]([C:27]2[C:28]3[CH:34]=[CH:33][CH:32]=[CH:31][C:29]=3[S:30][C:26]=2[C:23]2[CH:22]=[CH:21][C:20]([O:19][CH2:18][CH2:17][N:12]3[CH2:16][CH2:15][CH2:14][CH2:13]3)=[CH:25][CH:24]=2)=[O:36])=[CH:38][CH:39]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 769801-(2-Hydroxyethyl)-2-pyrrolidinoneHCID 107182054-Fluorophenyl 2-[4-[2-(1-pyrrolidinyl)ethoxy]phenyl]benzo[b]thiophen-3-yl ketone

Product 1

HCID 183185242-[4-[2-(1-Pyrrolidinyl)ethoxy]phenyl]-benzo[b]thiophen-3-yl 4-[2-(2-Oxopyrrolidin-1-yl)ethoxy]-phenyl Ketone

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 57417360Sodium chloride; waterSolvent

Procedure

Sodium hydride (60% oil dispersion, 50 mg) was suspended in DMF (2.0 mL) and stirred at ambient temperature for 15 min under argon before 1-(2-hydroxyethyl)-2-pyrrolidinone (87 μL) was added. After stirring for 15 min, 4-fluorophenyl 2-[4-[2-(1-pyrrolidinyl)ethoxy]phenyl]-benzo[b]thiophen-3-yl ketone (223 mg) in 1 mL of DMF was introduced and the resulting solution was stirred at ambient temperature for 3.5 h. The reaction mixture was diluted with brine (50 mL) and extracted with EtOAc (3×50 mL). The combined organic layers were dried (Na2SO4) and concentrated under reduced pressure. Chromatography with Et3N:MeOH:EtOAc (5:5-10:90-85) afforded the product as a colorless oil (210 mg).

Workup

  1. additionwas added
  2. stirringthe resulting solution was stirred at ambient temperature for 3.5 h
  3. extractionextracted with EtOAc (3×50 mL)
  4. dry with materialThe combined organic layers were dried (Na2SO4)
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-761aecc1390749efaed20213ce9a6005
Source dataset
uspto-grants-2002_02
Patent number
US06350774B1

Reaction notes

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