Potassium Phosphate, Tribasic → HCID 59454961, compound

HRID 1401619Notes

Reaction equation

HRID 1401619 reaction equation
Br[C:2]([CH3:11])=[C:3]([C:5]1[CH:10]=[CH:9][N:8]=[CH:7][CH:6]=1)[CH3:4].P([O-])([O-])([O-])=O.[K+].[K+].[K+].N1CCC[C@H]1C(O)=O.[CH3:28][N:29]1[CH2:42][CH2:41][C:32]2[NH:33][C:34]3[CH:35]=[CH:36][C:37]([CH3:40])=[CH:38][C:39]=3[C:31]=2[CH2:30]1>CN(C=O)C.[Cu]I>[CH3:28][N:29]1[CH2:42][CH2:41][C:32]2[N:33](/[C:2](=[C:3](/[C:5]3[CH:10]=[CH:9][N:8]=[CH:7][CH:6]=3)\[CH3:4])/[CH3:11])[C:34]3[CH:35]=[CH:36][C:37]([CH3:40])=[CH:38][C:39]=3[C:31]=2[CH2:30]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 86644768HCID 86644768, compound

Product 1

HCID 59454961HCID 59454961, compound

Reagents, catalysts & solvents 2

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

Conditions

Temperature
85 °C

Procedure

4-(3-Bromobut-2-en-2-yl)pyridine (127 mg, 0.59 mmol) was dissolved in DMF (5 mL) and potassium phosphate (212 mg, 1 mmol) was added followed by copper (I) iodide (9.5 mg, 0.05 mmol) and L-proline (11.5 mg, 0.1 mmol). 2,3,4,5-tetrahydro-2,8-dimethyl-1H-pyrido[4,3-b]indole (100 mg, 0.5 mmol) was added and nitrogen gas purged for 2 min. The reaction mixture was stirred at 85° C. overnight. Water was added and the reaction mixture filtered to obtain the solid mass under vacuum. The crude product was purified on silica gel (100-200 mesh) using 0-10% MeOH:DCM as eluent. The compound was further purified through reverse phase chromatography. Yield: 5 mg (TFA salt). 1H NMR (CD3OD, free base) δ (ppm): 8.60 (d, 2H), 7.50 (d, 2H), 7.24 (s, 1H), 7.12 (d, 1H), 6.99 (d, 1H), 3.78 (s, 2H), 2.98 (m, 2H), 2.90 (m, 2H), 2.60 (s, 3H), 2.42 (s, 3H), 1.92 (s, 3H), 1.66 (s, 3H).

Workup

  1. customnitrogen gas purged for 2 min
  2. additionWater was added
  3. filtrationthe reaction mixture filtered
  4. customto obtain the solid mass under vacuum
  5. customThe crude product was purified on silica gel (100-200 mesh)
  6. customThe compound was further purified through reverse phase chromatography

Sources & evidence

ORD record
ord-498ed3c3d91f4258b835361f623f5415
Source dataset
uspto-grants-2014_12
Patent number
US08907097B2

Reaction notes

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