Potassium Carbonate → HCID 46199893, compound

HRID 1400566Notes

Reaction equation

HRID 1400566 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]([CH:11]=[C:12]([C:14]3[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=3)[CH3:13])[C:6]3[CH2:20][CH2:21][NH:22][CH2:23][C:5]=3[C:4]=2[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[F:30][CH2:31][CH2:32]I>C(#N)C.O>[F:30][CH2:31][CH2:32][N:22]1[CH2:21][CH2:20][C:6]2[N:7](/[CH:11]=[C:12](/[C:14]3[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=3)\[CH3:13])[C:8]3[CH:9]=[CH:10][C:2]([CH3:1])=[CH:3][C:4]=3[C:5]=2[CH2:23]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 69804Ethane, 1-fluoro-2-iodo-HCID 67310663HCID 67310663, compound

Product 1

HCID 46199893HCID 46199893, compoundYield 49.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

8-Methyl-5-(2-pyridin-4-yl-propenyl)-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (60 mg, 0.19 mmol) was dissolved in acetonitrile (1 mL). Potassium carbonate (82 mg, 0.9 mmol) and 1-Fluoro-2-iodo-ethane (45 mg, 0.25 mmol) were added and stirred at RT for 1 h. The reaction mixture was heated at 80° C. for 1 h. After 1 h the reaction mixture was cooled to RT, diluted with water (10 mL) and extracted with EtOAc (3×20 mL). The organic layer was dried over sodium sulfate and concentrated under vacuum to obtained 33 mg of desired product. 1H NMR (CD3OD, oxalate salt) δ (ppm): 8.62 (d, 2H), 7.80 (d, 2H), 7.42 (s, 1H), 7.36 (s, 1H), 7.10 (m, 2H), 5.05 (m, 1H), 4.92 (m, 1H), 4.65 (s, 2H), 3.82 (m, 3H), 3.78 (m, 1H), 3.20 (m, 2H), 2.42 (s, 3H), 2.05 (s, 3H).

Workup

  1. temperatureThe reaction mixture was heated at 80° C. for 1 h
  2. temperatureAfter 1 h the reaction mixture was cooled to RT
  3. extractionextracted with EtOAc (3×20 mL)
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-dabbe589d5d345509cff86d06d435171
Source dataset
uspto-grants-2014_12
Patent number
US08906925B2

Reaction notes

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