Phenacyl bromide → 2-(2,8-Dimethyl-3,4-dihydro-1H-pyrido[4,3-b]indol-5(2H)-yl)-1-phenylethanone

HRID 1773245Notes

Reaction equation

HRID 1773245 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][CH:25]=[CH:24][CH:23]=1)=[O:21]>CN1C(=O)CCC1>[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][CH:25]=[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

5

Reactant 3

HCID 6259Phenacyl bromideHCID 14797Potassium HydroxideHCID 2092911H-Pyrido[4,3-b]indole, 2,3,4,5-tetrahydro-2,8-dimethyl-

Product 1

HCID 497799092-(2,8-Dimethyl-3,4-dihydro-1H-pyrido[4,3-b]indol-5(2H)-yl)-1-phenylethanoneYield 3.1%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

2,8-Dimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (100 mg, 5 mmol) was dissolved in NMP (1 mL). KOH (280 mg, 5 mmol) was then added to it, followed by addition of 2-bromoacetophenone (208 mg, 1 mmol). The reaction was kept overnight at RT and was monitored by TLC and LC/MS. The reaction was quenched by adding water, and the compound extracted using EtOAc, which was washed with water (2-3×). The organic layer was dried over sodium sulfate and then concentrated to yield 10 mg of dark brown crude oil, which was then purified by column chromatography using 100-200 mesh silica in 5% MeOH:DCM. 1HNMR (CD3OD, TFA salt) d (ppm): 8.15 (m, 1H), 7.70 (m, 1H), 7.60 (m, 2H), 7.28 (d, 1H), 7.20 (m, 1H), 7.0 (m, 1H), 5.80 (m, 2H), 4.70 (m, 1H), 4.40 (m, 1H), 4.20 (m, 1H), 3.80 (m, 1H), 3.60 (m, 2H), 3.10 (s, 1H), 2.40 (s, 3H), 2.30 (m, 1H), 2.0 (m, 1H), 1.80 (m, 1H).

Workup

  1. customThe reaction was quenched
  2. additionby adding water
  3. extractionthe compound extracted
  4. washwas washed with water (2-3×)
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-50c396ae461a4125b0c69987792243ee
Source dataset
uspto-grants-2016_02
Patent number
US09255094B2

Reaction notes

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