Potassium Phosphate, Tribasic → HCID 51356100, compound

HRID 2167814Notes

Reaction equation

HRID 2167814 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:18]3[CH2:17][N:16]4[CH:11]([CH2:12][CH2:13][CH2:14][CH2:15]4)[CH2:10][C:9]=3[NH:8][C:5]2=[CH:6][CH:7]=1.N1CCC[C@H]1C(O)=O.[O-]P([O-])([O-])=O.[K+].[K+].[K+].Br[CH:36]=[C:37]([C:39]1[CH:44]=[CH:43][C:42]([F:45])=[CH:41][CH:40]=1)[CH3:38]>CN(C=O)C.[Cu]I>[F:45][C:42]1[CH:43]=[CH:44][C:39](/[C:37](/[CH3:38])=[CH:36]/[N:8]2[C:9]3[CH2:10][CH:11]4[N:16]([CH2:17][C:18]=3[C:4]3[C:5]2=[CH:6][CH:7]=[C:2]([CH3:1])[CH:3]=3)[CH2:15][CH2:14][CH2:13][CH2:12]4)=[CH:40][CH:41]=1

Participants

7

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 145742L-ProlineHCID 67036585HCID 67036585, compoundHCID 86644757(1-Bromoprop-1-en-2-yl)-4-fluorobenzene

Product 1

HCID 51356100HCID 51356100, compound

Reagents, catalysts & solvents 2

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

Procedure

2-Methyl-5,6,6a,7,8,9,10,12-octahydroindolo[2,3-b]quinolizine (100 mg, 0.416 mmol) was dissolved in DMF (5 mL). Copper (I) iodide (7.9 mg, 0.0416 mmol), L-proline (9.6 mg, 0.08 mmol) and K3PO4 (176 mg, 0.00832 mmol) were added and the reaction mixture was stirred for 10 min at RT. 1-(1-Bromoprop-1-en-2-yl)-4-fluorobenzene (107 mg, 0.005 mmol) was added dropwise and the reaction mixture was purged with nitrogen. The reaction mixture was heated at 85° C. overnight (prolonged heating in some cases was required). The 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). The product was further purified by reverse phase HPLC. Yield: 80 mg as TFA salt;

Workup

  1. customthe reaction mixture was purged with nitrogen
  2. temperatureThe reaction mixture was heated at 85° C. overnight (
  3. temperatureprolonged heating in some cases
  4. customThe DMF 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)
  8. customThe product was further purified by reverse phase HPLC

Sources & evidence

ORD record
ord-b9f7085a2a9f422db2d71a482ae1ca63
Source dataset
uspto-grants-2015_06
Patent number
US09045482B2

Reaction notes

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