Iodoethane → HCID 66803677, compound

HRID 1843985Notes

Reaction equation

HRID 1843985 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:8]2[NH:7][C:6]3[CH2:11][CH2:12][NH:13][C:14](=[O:15])[C:5]=3[C:4]=2[CH:3]=1.[H-].[Na+].[CH2:18](I)[CH3:19]>CN(C=O)C>[CH2:18]([N:7]1[C:8]2[CH:9]=[CH:10][C:2]([F:1])=[CH:3][C:4]=2[C:5]2[C:14](=[O:15])[NH:13][CH2:12][CH2:11][C:6]1=2)[CH3:19]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 19799247HCID 19799247, compound

Product 1

HCID 66803677HCID 66803677, compoundYield 21.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

8-Fluoro-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indol-1-one (I-59f: 500 mg, 2.44 mmol) in DMF (200 mL) was reacted with 60% NaH (196 mg, 8.16 mmol) and ethyl iodide (456 mg, 2.92 mmol) to afford the crude product. The reaction mass was quenched with chilled water and extracted with ethyl acetate. The organic layer was washed with water, brine solution, dried over Na2SO4 and concentrated to afford the crude product. Purification by column chromatography on silica gel (1% methanol in DCM) afforded 120 mg of the product (21.2% yield).

Workup

  1. customto afford the crude product
  2. customThe reaction mass was quenched with chilled water
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water, brine solution
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customto afford the crude product
  8. customPurification by column chromatography on silica gel (1% methanol in DCM)

Sources & evidence

ORD record
ord-9e7539c2ee8043ab976cc8783e795160
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

Loading…