Potassium Hydroxide → HCID 49779911, compound

HRID 1773248Notes

Reaction equation

HRID 1773248 reaction equation
[CH3:1][N:2]1[CH2:15][CH2:14][C:5]2[NH:6][C:7]3[CH:8]=[CH:9][C:10]([CH3:13])=[CH:11][C:12]=3[C:4]=2[CH2:3]1.[OH-].[K+].Br[CH2:19][C:20]([C:22]1[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=1)=[O:21]>CN1C(=O)CCC1.O>[CH3:1][N:2]1[CH2:15][CH2:14][C:5]2[N:6]([CH2:19][C:20]([C:22]3[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=3)=[O:21])[C:7]3[CH:8]=[CH:9][C:10]([CH3:13])=[CH:11][C:12]=3[C:4]=2[CH2:3]1

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 967492-Bromo-1-(4-fluorophenyl)ethan-1-oneHCID 2092911H-Pyrido[4,3-b]indole, 2,3,4,5-tetrahydro-2,8-dimethyl-

Product 1

HCID 49779911HCID 49779911, compoundYield 11.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent2×

Procedure

To a solution of 2,8-dimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (7 g, 0.032 mol) in 3 mL of NMP, KOH (12.7 g, 0.226 mol) was added at RT. The reaction mixture was stirred well at RT for 20 min. Then a solution of 2-bromo-1-(4-fluorophenyl)ethanone (6.5 g, 0.032 mol) in 2 mL NMP was added dropwise into the reaction mixture at RT over 2-4 h. The reaction was monitored by LCMS and TLC. The reaction mixture was diluted with water and extracted with EtOAc. The organic layer was dried over sodium sulfate and concentrated under reduced pressure. The residue obtained was purified by column chromatography, providing the desired product (1.2 g, 11.02%). 1HNMR (CDCl3, TFA salt) d (ppm): 8.18-8.01 (m, 2H), 7.71 (s, 1H), 7.30 (s, 1H), 7.22-7.10 (m, 2H), 7.00 (d, 1H), 3.60-3.31 (m, 4H), 3.20-3.06 (m, 2H), 2.85-2.70 (m, 2H), 2.45 (s, 6H).

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue obtained
  5. customwas purified by column chromatography

Sources & evidence

ORD record
ord-3969664729be49c08013ac5aca74c0cf
Source dataset
uspto-grants-2016_02
Patent number
US09255094B2

Reaction notes

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