HCID 18318446, compound → HCID 21182946, compound

HRID 1387100Notes

Reaction equation

HRID 1387100 reaction equation
Br[C:2]1[CH:31]=[CH:30][C:5]([CH2:6][C:7]2[C:8]3[CH:29]=[CH:28][CH:27]=[CH:26][C:9]=3[S:10][C:11]=2[C:12]2[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH2:20][N:21]3[CH2:25][CH2:24][CH2:23][CH2:22]3)=[CH:14][CH:13]=2)=[CH:4][CH:3]=1.[C:32]([Cu])#[N:33]>CN(C=O)C>[C:32]([C:2]1[CH:3]=[CH:4][C:5]([CH2:6][C:7]2[C:8]3[CH:29]=[CH:28][CH:27]=[CH:26][C:9]=3[S:10][C:11]=2[C:12]2[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH2:20][N:21]3[CH2:25][CH2:24][CH2:23][CH2:22]3)=[CH:14][CH:13]=2)=[CH:30][CH:31]=1)#[N:33]

Participants

4

Reactant 2

HCID 18318446HCID 18318446, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 21182946HCID 21182946, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-(4-Bromobenzyl)-2-[4-[2-(1-pyrrolidinyl)ethoxy]phenyl]benzo[b]thiophene (300 mg, 0.61 mmol) in DMF (5 mL) was treated with CuCN (135 mg) at reflux for 3 h. The cooled reaction mixture was extracted with EtOAc (3×50 mL), with water (50 mL) washing. The combined organic layers were dried (Na2SO4) and concentrated under reduced pressure. Chromatography with Et3N:MeOH:EtOAc (5:5:90) afforded the product (90 mg, 34%).

Workup

  1. temperatureat reflux for 3 h
  2. customThe cooled reaction mixture
  3. extractionwas extracted with EtOAc (3×50 mL), with water (50 mL)
  4. washwashing
  5. dry with materialThe combined organic layers were dried (Na2SO4)
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8a9a88968a7146dcabc741a2ff03e456
Source dataset
uspto-grants-2001_07
Patent number
US06265575B1

Reaction notes

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