Sodium hydride → 7,10-Dichloro-1,2,3,4,5,6-hexahydro-3-methyl-6-(2-(6-methylpyridin-3-yl)ethyl)azepino[4,5-b]indole

HRID 2408743Notes

Reaction equation

HRID 2408743 reaction equation
[Cl:1][C:2]1[C:10]2[NH:9][C:8]3[CH2:11][CH2:12][N:13]([CH3:16])[CH2:14][CH2:15][C:7]=3[C:6]=2[C:5]([Cl:17])=[CH:4][CH:3]=1.[H-].[Na+].CC1C=CC(S(O[CH2:31][CH2:32][C:33]2[CH:34]=[N:35][C:36]([CH3:39])=[CH:37][CH:38]=2)(=O)=O)=CC=1>CN(C=O)C>[Cl:1][C:2]1[C:10]2[N:9]([CH2:31][CH2:32][C:33]3[CH:34]=[N:35][C:36]([CH3:39])=[CH:37][CH:38]=3)[C:8]3[CH2:11][CH2:12][N:13]([CH3:16])[CH2:14][CH2:15][C:7]=3[C:6]=2[C:5]([Cl:17])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 682839377,10-Dichloro-1,2,3,4,5,6-hexahydro-3-methylazepino[4,5-b]indoleHCID 866581512-(6-Methylpyridin-3-yl)ethyl 4-methylbenzenesulfonate

Product 1

HCID 710076037,10-Dichloro-1,2,3,4,5,6-hexahydro-3-methyl-6-(2-(6-methylpyridin-3-yl)ethyl)azepino[4,5-b]indole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 7,10-dichloro-1,2,3,4,5,6-hexahydro-3-methylazepino[4,5-b]indole (200 mg, 0.746 mmol) in DMF (2 mL), sodium hydride (90 mg, 2.25 mmol) was added. After stirring at 60° C. for 30 min., 2-(6-methylpyridin-3-yl)ethyl 4-methylbenzenesulfonate (543 mg, 1.86 mmol) was added to the reaction mixture and the reaction mixture was stirred at the same temperature for 40 min. The progress of reaction was monitored by TLC and LCMS. The reaction mixture was quenched with water and extracted with EtOAc. The organic layer was washed with water, dried over anhydrous sodium sulfate and concentrated to obtain the residue that was purified by reverse phase HPLC to obtain 7,10-dichloro-1,2,3,4,5,6-hexahydro-3-methyl-6-(2-(6-methylpyridin-3-yl)ethyl)azepino[4,5-b]indole. 1H NMR TFA:—CD3OD: 8.4 (s, 1H), 8.1 (d, 1H), 7.75 (d, 1H), 7.0 (q, 2H), 4.8 (m, 1H), 4.0 (m, 1H), 3.8 (m, 2H), 3.4 (m, 3H), 3.3 (m, 2H), 3.2 (t, 3H), 3.0 (s, 3H), 2.7 (s, 3H).

Workup

  1. stirringthe reaction mixture was stirred at the same temperature for 40 min
  2. customThe progress of reaction
  3. customThe reaction mixture was quenched with water
  4. extractionextracted with EtOAc
  5. washThe organic layer was washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated
  8. customto obtain the residue that
  9. customwas purified by reverse phase HPLC

Sources & evidence

ORD record
ord-1512e4d25a9c48f6916679f40e3b706f
Source dataset
uspto-grants-2014_08
Patent number
US08815843B2

Reaction notes

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