Water → HCID 49779779, compound

HRID 1773258Notes

Reaction equation

HRID 1773258 reaction equation
[CH3:1][N:2]1[CH2:15][CH:14]([CH3:16])[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+].[F:19][C:20]([F:30])([F:29])[C:21]1[CH:26]=[CH:25][C:24]([CH:27]=[CH2:28])=[CH:23][N:22]=1.O>CN1CCCC1=O>[CH3:1][N:2]1[CH2:15][CH:14]([CH3:16])[C:5]2[N:6]([CH2:28][CH2:27][C:24]3[CH:23]=[N:22][C:21]([C:20]([F:30])([F:19])[F:29])=[CH:26][CH:25]=3)[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 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 574168485-Ethenyl-2-(trifluoromethyl)pyridineHCID 66612299HCID 66612299, compound

Product 1

HCID 49779779HCID 49779779, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To a solution of 2,3,4,5-tetrahydro-2,4,8-trimethyl-1H-pyrido[4,3-b]indole (200 mg, 0.934 mmol) in N-methyl-2-pyrolidone (2.5 mL) was added powdered KOH (463 mg, 8.27 mmol) and allow to stir for 10 min at RT. 2-Trifluoromethyl-5-vinyl pyridine (323 mg, 1.87 mmol) was added and stirred further for 12 h at RT. The reaction was monitored by TLC. After completion of reaction, water (10 mL) was added and the mixture filtered. Water was added to the filtrate and the product extracted with EtOAc (50 mL). The organic layer was dried over sodium sulfate, evaporated in vacuum and purified by HPLC to obtain the product.

Workup

  1. stirringstirred further for 12 h at RT
  2. additionwas added
  3. filtrationthe mixture filtered
  4. additionWater was added to the filtrate
  5. extractionthe product extracted with EtOAc (50 mL)
  6. dry with materialThe organic layer was dried over sodium sulfate
  7. customevaporated in vacuum
  8. custompurified by HPLC
  9. customto obtain the product

Sources & evidence

ORD record
ord-05a1ea8b5e004a8cb770b8f13e2dfd89
Source dataset
uspto-grants-2016_02
Patent number
US09255094B2

Reaction notes

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