N,N'-Dimethylethylenediamine → HCID 69058741, compound

HRID 2100570Notes

Reaction equation

HRID 2100570 reaction equation
[O:1]=[C:2]1[C:11]2[C:10]([C:12]([F:15])([F:14])[F:13])=[CH:9][CH:8]=[CH:7][C:6]=2[C@H:5]2[CH2:16][N:17]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:18][C@H:4]2[NH:3]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].I[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.CNCCNC>C1(C)C=CC=CC=1.[Cu]I>[O:1]=[C:2]1[C:11]2[C:10]([C:12]([F:14])([F:15])[F:13])=[CH:9][CH:8]=[CH:7][C:6]=2[C@H:5]2[CH2:16][N:17]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:18][C@H:4]2[N:3]1[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

7

Reactant 4

HCID 8070N,N'-DimethylethylenediamineHCID 11575IodobenzeneHCID 62657Potassium Phosphate, TribasicHCID 69056519HCID 69056519, compound

Product 1

HCID 69058741HCID 69058741, compoundYield 80%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
90 °C

Procedure

To a solution of (±)-cis-tert-butyl 5-oxo-6-(trifluoromethyl)-3,3a,4,5-tetrahydro-1H-pyrrolo[3,4-c]isoquinoline-2(9bH)-carboxylate from Example 1, Part H (50 mg, 0.14 mmol) in 4 mL of toluene in a screw-cap vial was added copper (I) iodide (2.6 mg, 0.014 mmol) and potassium phosphate (65 mg, 0.31 mmol). The reaction was degassed with a stream of argon for several minutes, and then there was added iodobenzene (17 μL, 0.154 mmol) and N,N′-dimethylethylenediamine (3.0 μL, 0.028 mmol). The reaction was allowed to stir at 90° C. in the sealed vial for 18 h. The reaction was quenched with water, diluted with EtOAc and washed with 1N HCl, sat'd aq NaHCO3 and brine, dried (MgSO4) and concentrated in vacuo. The residue was purified by flash chromatography (230-400 mesh silica gel, elution with 2:1 hexane/EtOAc) to afford 48 mg (80%) of the title compound. LRMS (ESI): 377.23 (M+H—C4H8)+.

Workup

  1. customThe reaction was degassed with a stream of argon for several minutes
  2. customThe reaction was quenched with water
  3. additiondiluted with EtOAc
  4. washwashed with 1N HCl
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chromatography (230-400 mesh silica gel, elution with 2:1 hexane/EtOAc)

Sources & evidence

ORD record
ord-4beb4a64095a456d90c6774eea7d3700
Source dataset
uspto-grants-2009_08
Patent number
US07572805B2

Reaction notes

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