N,N'-Dimethylethylenediamine → HCID 69316801, compound

HRID 269961Notes

Reaction equation

HRID 269961 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:21][CH2:20][C:11]2[NH:12][C:13]3[CH:14]=[CH:15][C:16]([F:19])=[CH:17][C:18]=3[C:10]=2[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[O-]P([O-])([O-])=O.[K+].[K+].[K+].I[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.CNCCNC>C1(C)C=CC=CC=1.[Cu]I>[C:1]([O:5][C:6]([N:8]1[CH2:21][CH2:20][C:11]2[N:12]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[C:13]3[CH:14]=[CH:15][C:16]([F:19])=[CH:17][C:18]=3[C:10]=2[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 8070N,N'-DimethylethylenediamineHCID 11575IodobenzeneHCID 62657Potassium Phosphate, TribasicHCID 69312818HCID 69312818, compound

Product 1

HCID 69316801HCID 69316801, compoundYield 56.1%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
150 °C

Procedure

A mixture of 8-fluoro-1,3,4,5-tetrahydropyrido[4,3-b]indole-2-carboxylic acid tert-butyl ester (0.455 g, 1.57 mmol), CuI (0.012 g, 0.065 mmol) and K3PO4 (0.579 g, 2.73 mmol) was suspended in toluene (5 mL) under Ar. To this mixture was added iodobenzene (0.145 mL, 1.30 mmol) and N,N′-dimethylethylenediamine (0.028 mL, 0.26 mmol) and then the reaction vessel was quickly sealed and the mixture was heated with stirring at 150° C. (oil bath temperature) for 16 h. The cooled reaction mixture was subsequently filtered (Celite) and the filtrate was concentrated to dryness. The residue was purified by flash chromatography (SiO2/hexanes-ethyl acetate, 80:20 to 20:80) to give the title compound (0.267 g, 46%) as a white foam. 1H NMR (400 MHz, CDCl3) δ 7.51 (m, 2H), 7.41 (m, 1H), 7.33 (m, 2H), 7.15 (m, 2H), 6.87 (m, 1H), 4.66 (s, 2H), 3.77 (m, 2H), 2.70 (m, 2H), 1.51 (s, 9H); LCMS: m/e 367 (M+H)+.

Workup

  1. customthe reaction vessel was quickly sealed
  2. temperaturethe mixture was heated
  3. customThe cooled reaction mixture
  4. filtrationwas subsequently filtered (Celite)
  5. concentrationthe filtrate was concentrated to dryness
  6. customThe residue was purified by flash chromatography (SiO2/hexanes-ethyl acetate, 80:20 to 20:80)

Sources & evidence

ORD record
ord-eefb9adfeb8c44c4939e0187b95a4326
Source dataset
uspto-grants-2008_11
Patent number
US07449476B2

Reaction notes

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