8-chloro-2-methyl-1H,2H,3H,4H,5H-pyrido(4,3-b)indole → HCID 49779445, compound

HRID 1773280Notes

Reaction equation

HRID 1773280 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+].[CH3:18][C:19]1([C:22]2[CH:27]=[N:26][CH:25]=[CH:24][N:23]=2)[CH2:21][O:20]1>CN(C=O)C>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]([CH2:18][C:19]([C:22]3[CH:27]=[N:26][CH:25]=[CH:24][N:23]=3)([OH:20])[CH3:21])[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 86665936HCID 86665936, compound

Product 1

HCID 49779445HCID 49779445, compoundYield 74.1%

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 (1.0 g, 4.54 mmol) in DMF (10 mL) was added sodium hydride (600 mg, 13.63 mmol). After stirring for 10 min at RT, 2-(2-methyl oxiranyl)pyrazine (804 mg, 5.9 mmol) was added dropwise at 0-10° C. and the reaction mixture was stirred at RT for 16 h. The reaction mixture was poured into ice water and extracted with EtOAc (3×150 mL). The organic layer was washed with water, dried over anhydrous sodium sulfate and concentrated to afford crude product, which was crystallized in ether-hexane to yield a yellow solid product as the free base (1.2 g). 1H NMR (DMSO, Oxalate salt) d (ppm): 8.65 (s, 1H), 8.55 (s, 1H), 8.50 (d, 1H), 7.42 (s, 1H), 7.05 (d, 1H), 6.95 (d, 1H), 4.40 (m, 4H), 3.20 (m, 2H), 3.0 (m, 2H), 2.90 (s, 3H), 1.58 (s, 3H).

Workup

  1. stirringthe reaction mixture was stirred at RT for 16 h
  2. extractionextracted with EtOAc (3×150 mL)
  3. washThe organic layer was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customto afford crude product, which
  7. customwas crystallized in ether-hexane

Sources & evidence

ORD record
ord-631b8d40fcbe472bb1abc148ccaa8f2c
Source dataset
uspto-grants-2016_02
Patent number
US09255094B2

Reaction notes

Loading…