Potassium Phosphate, Tribasic → HCID 59455021, compound

HRID 1400485Notes

Reaction equation

HRID 1400485 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.N1CCC[C@H]1C(O)=O.P([O-])([O-])([O-])=O.[K+].[K+].[K+].Br[CH:33]=[C:34]([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][N:37]=1)[CH3:35]>CN(C=O)C.[Cu]I>[CH3:1][N:2]1[CH2:15][CH2:14][C:5]2[N:6](/[CH:33]=[C:34](/[C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][N:37]=3)\[CH3:35])[C:7]3[CH:8]=[CH:9][C:10]([CH3:13])=[CH:11][C:12]=3[C:4]=2[CH2:3]1

Participants

7

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 145742L-ProlineHCID 2092911H-Pyrido[4,3-b]indole, 2,3,4,5-tetrahydro-2,8-dimethyl-HCID 85185762HCID 85185762, compound

Product 1

HCID 59455021HCID 59455021, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolvent

Procedure

2,8-Dimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (700 mg, 3.5 mmol) was dissolved in DMF. Copper (I) iodide, L-proline (0.116 g, 0.7 mmol) and potassium phosphate (1.484 g, 7 mmol) were added and the reaction mixture was stirred for 10 min. at RT. 2-(1-Bromoprop-1-en-2-yl)pyridine (1.03 g, 5.25 mmol) was added dropwise and the reaction mixture was purged with nitrogen. The reaction mixture was heated overnight at 85° C. (prolonged heating in some cases was required). DMF was evaporated under reduced pressure, the residue was diluted with water and the solid was filtered. The solid material was purified by silica gel chromatography (100-200 mesh). 1H NMR (CDCl3, HCl salt) δ (ppm): 8.62 (d, 1H), 7.78 (t, 1H), 7.60 (s, 1H), 7.50 (d, 1H), 7.28 (m, 1H), 7.18 (s, 1H), 7.10 (d, 1H), 7.05 (d, 1H), 4.40 (s, 2H), 3.50 (m, 2H), 3.20 (m, 2H), 2.95 (s, 3H), 2.42 (s, 3H), 2.05 (s, 3H).

Workup

  1. customthe reaction mixture was purged with nitrogen
  2. temperatureThe reaction mixture was heated overnight at 85° C. (
  3. temperatureprolonged heating in some cases
  4. customDMF was evaporated under reduced pressure
  5. additionthe residue was diluted with water
  6. filtrationthe solid was filtered
  7. customThe solid material was purified by silica gel chromatography (100-200 mesh)

Sources & evidence

ORD record
ord-70e50fcd9372478f89d637c5614d4207
Source dataset
uspto-grants-2014_12
Patent number
US08906925B2

Reaction notes

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