Water → HCID 49779839, compound

HRID 1773252Notes

Reaction equation

HRID 1773252 reaction equation
[CH3:1][N:2]1[CH:15]([CH3:16])[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+].[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[CH:15]([CH3:16])[CH2:14][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 666120872,3,8-Trimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole

Product 1

HCID 49779839HCID 49779839, compoundYield 5.5%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To a solution of 2,3,8-trimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (200 mg, 0.935 mmol) in N-methyl-2-pyrolidone (2.5 mL) was added powdered KOH (463 mg, 8.27 mmol) and stirred for 10 min at RT. 2-Trifluoromethyl-5-vinyl pyridine (300 mg, 1.73 mmol) was added and stirred further for 4 h at RT. The reaction was monitored by TLC. After completion of reaction, water (10 mL) was added to the mixture, which was then filtered. Water was added to the filtrate, which was then extracted with EtOAc (50 mL). The organic layer was dried over sodium sulfate, concentrated in vacuum and the residue purified by column chromatography (100-200 mesh silica gel) to obtain 20 mg of desired compound. The free base compound was converted into the oxalate salt. 1HNMR (CDCl3, Freebase) d (ppm): 8.40 (s, 1H), 7.45 (d, 1H), 7.25 (m, 2H), 7.10 (d, 1H), 6.98 (d, 1H), 4.22 (t, 2H), 3.82 (d, 1H), 3.62 (d, 1H), 3.50 (m, 1H), 3.10 (t, 2H), 2.80 (m, 1H), 2.45 (s, 3H), 2.38 (s, 3H), 2.10 (dd, 1H), 1.10 (d, 3H).

Workup

  1. stirringstirred further for 4 h at RT
  2. additionwas added to the mixture, which
  3. filtrationwas then filtered
  4. additionWater was added to the filtrate, which
  5. extractionwas then extracted with EtOAc (50 mL)
  6. dry with materialThe organic layer was dried over sodium sulfate
  7. concentrationconcentrated in vacuum
  8. customthe residue purified by column chromatography (100-200 mesh silica gel)

Sources & evidence

ORD record
ord-5fdb411a16a24d58bbd332a5558e0ef8
Source dataset
uspto-grants-2016_02
Patent number
US09255094B2

Reaction notes

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