HCID 21182946, compound → HCID 21182659, compound

HRID 1387101Notes

Reaction equation

HRID 1387101 reaction equation
[C:1]([C:3]1[CH:32]=[CH:31][C:6]([CH2:7][C:8]2[C:9]3[CH:30]=[CH:29][CH:28]=[CH:27][C:10]=3[S:11][C:12]=2[C:13]2[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21][N:22]3[CH2:26][CH2:25][CH2:24][CH2:23]3)=[CH:15][CH:14]=2)=[CH:5][CH:4]=1)#[N:2].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[NH2:2][CH2:1][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][C:8]2[C:9]3[CH:30]=[CH:29][CH:28]=[CH:27][C:10]=3[S:11][C:12]=2[C:13]2[CH:14]=[CH:15][C:16]([O:19][CH2:20][CH2:21][N:22]3[CH2:23][CH2:24][CH2:25][CH2:26]3)=[CH:17][CH:18]=2)=[CH:31][CH:32]=1

Participants

4

Reactant 2

HCID 21182946HCID 21182946, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 21182659HCID 21182659, compoundYield 37.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-(4-Cyanobenzyl)-2-[4-[2-(1-pyrrolidinyl)ethoxy]phenyl]benzo[b]thiophene (50 mg, 0.114 mmol) in THF (2 mL) was treated with lithium aluminum hydride (40 mg) at ambient temperature under argon for 1 h. The reaction was quenched with water (0.5 mL) and a solution of NaOH (1.0 M, 0.5 mL). The stirring was continued for 15 min. The resulting mixture was diluted with brine (30 mL) and extracted with CH2Cl2 (3×30 mL). The combined organic layers were dried (Na2SO4) and concentrated under reduced pressure. Chromatography with Et3N:MeOH:EtOAc (10:40:50) afforded the product (19 mg, 37%).

Workup

  1. customThe reaction was quenched with water (0.5 mL)
  2. additionThe resulting mixture was diluted with brine (30 mL)
  3. extractionextracted with CH2Cl2 (3×30 mL)
  4. dry with materialThe combined organic layers were dried (Na2SO4)
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3b19c2849f7e461ba67cf8b56abc4a8d
Source dataset
uspto-grants-2001_07
Patent number
US06265575B1

Reaction notes

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