1,1-Dichloroethane → HCID 25213242, compound

HRID 2089576Notes

Reaction equation

HRID 2089576 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH3:17])[CH:5]=[C:6]2[C:10]=1[NH:9][C:8]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=1)=[CH:7]2.[C:18]1(=O)[CH2:22][CH2:21][CH2:20][CH2:19]1.ClC(Cl)C.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C([O-])(O)=O.[Na+]>[CH:18]1([NH:1][C:2]2[CH:3]=[C:4]([CH3:17])[CH:5]=[C:6]3[C:10]=2[NH:9][C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)=[CH:7]3)[CH2:22][CH2:21][CH2:20][CH2:19]1

Participants

6

Reactant 4

HCID 63651,1-DichloroethaneHCID 8452CyclopentanoneHCID 5049666Sodium triacetoxyborohydrideHCID 68474590HCID 68474590, compound

Product 1

HCID 25213242HCID 25213242, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

7-Amino-5-methyl-2-(pyridin-2-yl)-1H-indole (5 g, 22.4 mmol) prepared in Step A and cyclopentanone (1.88 g, 22.4 mmol) were added to dichloroethane (50 mL). NaBH(OAc)3 (9.5 g, 44.8 mmol) was added thereto, and the mixture was stirred for 12 h at room temperature. After completion of the reaction, the reaction mixture was diluted with saturated aqueous NaHCO3 solution, and extracted with dichloromethane and EtOAc. The extracted organic material was washed with water and aqueous NaCl solution, and dried over MgSO4. The solvent was removed under reduced pressure, and the residue was purified by column chromatography (eluent EtOAc/n-Hex=1/5) to give the title compound (3.77 g, Yield 58%).

Workup

  1. customAfter completion of the reaction
  2. extractionextracted with dichloromethane and EtOAc
  3. washThe extracted organic material was washed with water and aqueous NaCl solution
  4. dry with materialdried over MgSO4
  5. customThe solvent was removed under reduced pressure
  6. customthe residue was purified by column chromatography (eluent EtOAc/n-Hex=1/5)

Sources & evidence

ORD record
ord-b92734334a954007a1faf9ab81148160
Source dataset
uspto-grants-2013_05
Patent number
US08436038B2

Reaction notes

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