8-chloro-2-methyl-1H,2H,3H,4H,5H-pyrido(4,3-b)indole → HCID 59455121, compound

HRID 1400602Notes

Reaction equation

HRID 1400602 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]2[NH:7][C:6]3[CH2:11][CH2:12][N:13]([CH3:15])[CH2:14][C:5]=3[C:4]=2[CH:3]=1.[H-].[Na+].[C:18]1([C:24]2([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH2:26][O:25]2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CN(C=O)C>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]([CH2:26][C:24]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[OH:25])[C:6]3[CH2:11][CH2:12][N:13]([CH3:15])[CH2:14][C:5]=3[C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 196158-chloro-2-methyl-1H,2H,3H,4H,5H-pyrido(4,3-b)indoleHCID 24758Sodium hydrideHCID 935642,2-Diphenyloxirane

Product 1

HCID 59455121HCID 59455121, compoundYield 63.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 8-chloro 2-methyl-2,3,4,5-tetrahydro-1H-pyrido (4,3-b) indole (800 g, 3.6 mmol) in 8 mL DMF, was added sodium hydride [60% dispersion in oil] (436 mg, 10.9 mmol) and the reaction mixture was stirred for 5 min. 2,2-Diphenyl oxirane (1.06 g, 5.4 mmol) was added dropwise at RT and reaction mixture stirred at RT for 16 h. The reaction mixture was poured into ice water and the desired compound extracted with EtOAc (3×200 mL). The organic layer was washed with water, dried over sodium sulfate and concentrated under vacuum to obtain the crude product, which was crystallized in ether (50 mL) to obtain 950 mg of white solid product as the free base. 100 mg free base was converted to HCL salt. 1H NMR (DMSO, HCl salt) δ (ppm): 7.50 (m, 2H), 7.40 (s, 1H), 7.30 (m, 3H), 7.22 (m, 5H), 7.14 (d, 1H), 6.82 (d, 1H), 6.15 (bs, 1H), 4.82 (d, 2H), 4.55 (m, 1H), 4.38 (m, 1H), 4.20 (m, 1H), 3.56 (m, 1H), 3.20 (m, 2H), 2.86 (s, 3H).

Workup

  1. customreaction mixture
  2. stirringstirred at RT for 16 h
  3. extractionthe desired compound extracted with EtOAc (3×200 mL)
  4. washThe organic layer was washed with water
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under vacuum
  7. customto obtain the crude product, which
  8. customwas crystallized in ether (50 mL)

Sources & evidence

ORD record
ord-beb1cc2d0672409b9695cee24cbab2bb
Source dataset
uspto-grants-2014_12
Patent number
US08906925B2

Reaction notes

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