Dimethylformamide → HCID 59454976, compound

HRID 1401608Notes

Reaction equation

HRID 1401608 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]2[NH:7][C:6]3[CH2:11][CH2:12][N:13]([CH3:15])[CH2:14][C:5]=3[C:4]=2[CH:3]=1.[NH:16]1[CH2:23][CH2:22]C[C@H:17]1C(O)=O.[O-]P([O-])([O-])=O.[K+].[K+].[K+].[CH3:32][C:33]1N=CC=N[CH:38]=1.C[N:40]([CH:42]=O)[CH3:41]>[Cu]I>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7](/[CH:32]=[C:33](/[C:41]3[CH:17]=[N:16][C:23]([CH3:22])=[CH:42][N:40]=3)\[CH3:38])[C:6]3[CH2:11][CH2:12][N:13]([CH3:15])[CH2:14][C:5]=3[C:4]=2[CH:3]=1

Participants

7

Reactant 5

HCID 6228DimethylformamideHCID 79762-MethylpyrazineHCID 196158-chloro-2-methyl-1H,2H,3H,4H,5H-pyrido(4,3-b)indoleHCID 62657Potassium Phosphate, TribasicHCID 145742L-Proline

Product 1

HCID 59454976HCID 59454976, compound

Reagents, catalysts & solvents 1

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Catalyst

Conditions

Temperature
90 °C

Procedure

8-Chloro 2-methyl-2,3,4,5-tetrahydro-1H-pyrido (4,3-b) indole (200 mg, 0.909 mmol), copper (I) iodide (17.2 mg, 0.09 mmol), L-proline (20.9 mg, 0.1818 mmol), Potassium phosphate tribasic (385 mg, 1.818 mmol) were charged in DMF (3 mL) and stirred for 5 min. 2-(2-bromo-1-methyl-vinyl))-5-methyl pyrazine (210 mg, 0.0.999 mmol) was added and nitrogen gas purged into the reaction mixture for a min. The resulting solution was stirred at RT for 5 min followed by heating at 90° C. for 14 h. After completion of the reaction, DMF was evaporated, water was added and the reaction mixture filtered. The crude product was purified by reverse phase HPLC to obtain 40 mg desired product. 1H NMR (CDCl3, free base) δ (ppm): 8.70 (s, 1H), 8.50 (s, 1H), 7.58 (s, 1H), 7.40 (s, 1H), 7.18 (d, 1H), 7.10 (d, 1H), 3.90 (s, 2H), 3.10 (m, 2H), 3.0 (m, 2H), 2.75 (s, 3H), 2.60 (s, 3H), 2.05 (s, 3H).

Workup

  1. customnitrogen gas purged into the reaction mixture for a min
  2. stirringThe resulting solution was stirred at RT for 5 min
  3. customAfter completion of the reaction, DMF
  4. customwas evaporated
  5. additionwater was added
  6. filtrationthe reaction mixture filtered
  7. customThe crude product was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-d7b63ecedc1f47378a794370f78050c6
Source dataset
uspto-grants-2014_12
Patent number
US08907097B2

Reaction notes

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