Potassium Hydroxide → HCID 49779836, compound

HRID 1773253Notes

Reaction equation

HRID 1773253 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+].C([C:20]1[CH:25]=[C:24]([C:26]([CH3:28])=[CH2:27])[CH:23]=[CH:22][N:21]=1)=C>CN1C(=O)CCC1.O>[CH3:1][N:2]1[CH2:15][CH2:14][C:5]2[N:6]([CH2:27][CH:26]([C:24]3[CH:23]=[CH:22][N:21]=[CH:20][CH:25]=3)[CH3:28])[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 2092911H-Pyrido[4,3-b]indole, 2,3,4,5-tetrahydro-2,8-dimethyl-HCID 66611985HCID 66611985, compound

Product 1

HCID 49779836HCID 49779836, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

2,8-Dimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (100 mg, 0.5 mmol) was dissolved in NMP (3 mL) and KOH (280 mg, 5 mmol) was added with vinyl 4-(prop-1-en-2-yl)pyridine (178 mg, 1.5 mmol). The reaction was stirred at RT for 14 h. After completion, the mixture was diluted with water and extracted with EtOAc. The organic layer was washed with water, concentrated and the residue purified by HPLC. 1HNMR (CD3OD, Oxalate salt) d (ppm): 8.4 (d, 2H), 7.25-7.15 (m, 4H), 7.05 (d, 1H), 4.4-4.2 (m, 3H), 3.80-3.79 (m, 2H), 3.50-3.40 (m, 2H), 3.15 (m, 1H), 3.05 (s, 3H) 2.70 (m, 1H), 2.40 (s, 3H), 1.40 (d, 3H).

Workup

  1. extractionextracted with EtOAc
  2. washThe organic layer was washed with water
  3. concentrationconcentrated
  4. customthe residue purified by HPLC

Sources & evidence

ORD record
ord-0905330e77f549d38ce48e318eeb1930
Source dataset
uspto-grants-2016_02
Patent number
US09255094B2

Reaction notes

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