Ethylenediamine → HCID 21081622, compound

HRID 2117153Notes

Reaction equation

HRID 2117153 reaction equation
C[Si](C)(C)CCOC[N:7]1[C:11]2=[N:12][CH:13]=[CH:14][CH:15]=[C:10]2[CH:9]=[CH:8]1.[Cl-].[NH4+:19].CCCC[N+:24]([CH2:33][CH2:34][CH2:35][CH3:36])([CH2:29]CCC)CCCC.[F-:37].[CH2:38](N)[CH2:39]N.[CH2:42]1[CH2:46][O:45][CH2:44][CH2:43]1>CCOC(C)=O.[Zn].CO>[F:37][C:38]1[CH:39]=[C:44]([NH2:19])[CH:43]=[CH:42][C:46]=1[O:45][C:15]1[CH:14]=[CH:13][N:12]=[C:11]2[NH:7][CH:8]=[C:9]([C:35]3[CH:36]=[CH:29][N:24]=[CH:33][CH:34]=3)[C:10]=12

Participants

9

Reactant 5

HCID 3301EthylenediamineHCID 8028Tetrahydrofuran2×HCID 25517Ammonium ChlorideHCID 2724141Tetrabutylammonium FluorideHCID 584313511-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 21081622HCID 21081622, compoundYield 81%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of 4-(2-fluoro-4-nitrophenoxy)-3-(pyridin-4-yl)-1-((2-(trimethylsilyl)ethoxy)methyl-1H-pyrrolo[2,3-b]pyridine (237 mg, 0.49 mmol) in a mixed solvent (8 mL of MeOH and 4 mL of THF) were added ammonium chloride (131 mg, 2.49 mmol, EMC) and zinc dust (163 mg, 2.49 mmol, Aldrich). The reaction mixture was stirred at room temperature for 3 h, diluted with EtOAc (40 mL), and filtered through a pad of Celite®. The filtrate was concentrated in vacuo to give a solid. MS(ESI+) m/z 451.3 (M+H)+. The solid was dissolved in 15 mL of THF and treated with TBAF (4 mL, 1.0 M solution in THF, Aldrich) and ethane-1,2-diamine (0.4 mL, Aldrich). The reaction mixture was refluxed for 16 h, cooled to room temperature, diluted with EtOAc, washed with brine, dried (MgSO4), and concentrated in vacuo. The residue was purified by flash chromatography (SiO2, eluting with 2-5% MeOH in dichloromethane) to afford the desired product (127 mg, 81% for two steps). MS(ESI+) m/z 321.2 (M+H)+.

Workup

  1. filtrationfiltered through a pad of Celite®
  2. concentrationThe filtrate was concentrated in vacuo
  3. customto give a solid
  4. temperatureThe reaction mixture was refluxed for 16 h
  5. temperaturecooled to room temperature
  6. washwashed with brine
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by flash chromatography (SiO2, eluting with 2-5% MeOH in dichloromethane)

Sources & evidence

ORD record
ord-b7ce0653f45c46e6bfd1b498bdad332f
Source dataset
uspto-grants-2008_10
Patent number
US07439246B2

Reaction notes

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