Potassium Phosphate, Tribasic → HCID 53373013, compound

HRID 1499054Notes

Reaction equation

HRID 1499054 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.Br[C:17]1[N:21]([CH3:22])[CH:20]=[N:19][CH:18]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].N1CCC[C@H]1C(O)=O>CN(C=O)C.O.[Cu]I>[CH3:1][N:2]1[CH2:15][CH2:14][C:5]2[N:6]([C:17]3[N:21]([CH3:22])[CH:20]=[N:19][CH:18]=3)[C:7]3[CH:8]=[CH:9][C:10]([CH3:13])=[CH:11][C:12]=3[C:4]=2[CH2:3]1

Participants

8

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 145742L-ProlineHCID 2092911H-Pyrido[4,3-b]indole, 2,3,4,5-tetrahydro-2,8-dimethyl-HCID 15152585-Bromo-1-methyl-1H-imidazole

Product 1

HCID 53373013HCID 53373013, compoundYield 2.7%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 2,8-dimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (0.4 g, 2 mmol), 5-bromo-1-methyl-1H-imidazole (0.644 g, 4 mmol), K3PO4 (0.848 g, 4 mmol), CuI (38 mg, 0.2 mmol) and L-Proline (46 mg, 0.39 mmol) in dry DMF (6 mL) was stirred at 150° C. for 16 h. The reaction mixture was diluted with water and extracted with EtOAc. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford crude material, which was purified by reverse phase HPLC to yield 2,8-dimethyl-5-(3-methyl-3H-imidazol-4-yl)-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (15 mg). 1H NMR (HCl salt, CD3OD) δ (ppm): 9.20 (s, 1H), 8.0 (s, 1H), 7.40 (s, 1H), 7.20 (d, 1H), 7.10 (d, 1H), 4.76 (d, 1H), 4.40 (d, 1H), 3.84 (m, 1H), 3.62 (m, 1H), 3.58 (d, 3H), 3.18 (s, 3H), 3.05 (m, 1H), 2.90 (m, 1H), 2.44 (s, 3H).

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customto afford crude material, which
  5. customwas purified by reverse phase HPLC

Sources & evidence

ORD record
ord-323eca1468cb4466882e4a49bc6028e3
Source dataset
uspto-grants-2015_12
Patent number
US09199985B2

Reaction notes

Loading…