N,N'-Dimethylethylenediamine → HCID 69057399, compound

HRID 2100633Notes

Reaction equation

HRID 2100633 reaction equation
[CH2:1]([C:3]1[CH:12]=[C:11]([CH3:13])[C:10]2[C:9](=[O:14])[NH:8][C@@H:7]3[CH2:15][N:16]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:17][C@H:6]3[C:5]=2[CH:4]=1)[CH3:2].P([O-])([O-])([O-])=O.[K+].[K+].[K+].I[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.CNCCNC>C1(C)C=CC=CC=1.[Cu]I>[CH2:1]([C:3]1[CH:12]=[C:11]([CH3:13])[C:10]2[C:9](=[O:14])[N:8]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[C@@H:7]3[CH2:15][N:16]([C:18]([O:20][C:21]([CH3:23])([CH3:22])[CH3:24])=[O:19])[CH2:17][C@H:6]3[C:5]=2[CH:4]=1)[CH3:2]

Participants

7

Reactant 4

HCID 8070N,N'-DimethylethylenediamineHCID 11575IodobenzeneHCID 62657Potassium Phosphate, TribasicHCID 69055271HCID 69055271, compound

Product 1

HCID 69057399HCID 69057399, compoundYield 41%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of (±)-trans-tert-butyl 8-ethyl-6-methyl-5-oxo-3,3a,4,5-tetrahydro-1H-pyrrolo[3,4-c]isoquinoline-2(9bH)-carboxylate from Example 74, Part A (50 mg, 0.15 mmol) in 2 mL of degassed toluene was added copper (I) iodide (2.1 mg, 0.011 mmol), potassium phosphate (70 mg, 0.33 mmol), iodobenzene (0.020 mL, 0.18 mmol) and N,N′-dimethylethylenediamine (0.0025 mL, 0.022 mmol). The mixture was stirred at 110° C. for 2 days. The reaction was cooled and quenched with 1N HCl and diluted with ethyl acetate. The organics were washed sequentially with sat'd aq. NaHCO3, and brine, dried (MgSO4), and concentrated. The residue was purified by flash chromatography (elution with 6:1 hexane/EtOAc) to afford 25 mg (41%) of the title compound as an oil. LRMS (ESI): 407.3 (M+H)+.

Workup

  1. temperatureThe reaction was cooled
  2. customquenched with 1N HCl
  3. additiondiluted with ethyl acetate
  4. washThe organics were washed sequentially with sat'd aq. NaHCO3, and brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography (elution with 6:1 hexane/EtOAc)

Sources & evidence

ORD record
ord-3a5635ead5884b319b48acbd1078873d
Source dataset
uspto-grants-2009_08
Patent number
US07572805B2

Reaction notes

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