Sodium hydride → HCID 49779653, compound

HRID 1773290Notes

Reaction equation

HRID 1773290 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:8]2[NH:7][C:6]3[CH2:11][CH2:12][N:13]([CH2:15][C:16]([F:19])([F:18])[F:17])[CH2:14][C:5]=3[C:4]=2[CH:3]=1.[H-].[Na+].CC1C=CC(S(O[CH2:33][CH2:34][C:35]2[CH:36]=[N:37][C:38]([CH3:41])=[CH:39][CH:40]=2)(=O)=O)=CC=1>CN(C=O)C>[CH3:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]([CH2:33][CH2:34][C:35]3[CH:36]=[N:37][C:38]([CH3:41])=[CH:39][CH:40]=3)[C:6]3[CH2:11][CH2:12][N:13]([CH2:15][C:16]([F:17])([F:19])[F:18])[CH2:14][C:5]=3[C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 66611929HCID 66611929, compoundHCID 866581512-(6-Methylpyridin-3-yl)ethyl 4-methylbenzenesulfonate

Product 1

HCID 49779653HCID 49779653, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 8-methyl-2-(2,2,2-trifluoroethyl)-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (100 mg, 0.372 mmol) in DMF (2 mL) were added sodium hydride (50 mg, 1.11 mmol) and 2-(6-methylpyridin-3-yl)ethyl 4-methylbenzenesulfonate (271.3 mg, 0.932 mmol). The reaction mixture was irradiated in a microwave reactor at 90° C. for 1 h. The reaction mixture was cooled to RT, quenched with water and extracted with EtOAc (3×10 mL). The organic layer was washed with water (2×10 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford crude material, which was purified by reverse phase HPLC. 1H NMR (CD3OD, TFA salt) d (ppm): 8.16 (s, 1H), 8.1 (d, 1H), 7.65 (d, 1H), 7.2 (s, 1H), 7.0 (d, 1H), 6.9 (d, 1H), 4.48 (s, 2H), 4.4 (t, 2H), 4.17 (q, 2H), 3.62 (t, 2H), 3.2 (t, 2H), 3.08 (t, 2H), 2.64 (s, 3H), 2.4 (s, 3H).

Workup

  1. customThe reaction mixture was irradiated in a microwave reactor at 90° C. for 1 h
  2. customquenched with water
  3. extractionextracted with EtOAc (3×10 mL)
  4. washThe organic layer was washed with water (2×10 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customto afford crude material, which
  8. customwas purified by reverse phase HPLC

Sources & evidence

ORD record
ord-df4a1df390b6494286c7a84be9af9700
Source dataset
uspto-grants-2016_02
Patent number
US09255094B2

Reaction notes

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