1,10-Phenanthroline → HCID 66893251, compound

HRID 1161998Notes

Reaction equation

HRID 1161998 reaction equation
I[C:2]1[C:10]2[O:9][CH:8]=[CH:7][C:6]=2[CH:5]=[C:4]([N+:11]([O-:13])=[O:12])[CH:3]=1.[N:14]12[CH2:21][CH2:20][CH:17]([CH2:18][CH2:19]1)[CH:16]([OH:22])[CH2:15]2.N1C2C(=CC=C3C=2N=CC=C3)C=CC=1>[Cu]I.C1(C)C=CC=CC=1>[N+:11]([C:4]1[CH:3]=[C:2]([O:22][CH:16]2[CH:17]3[CH2:20][CH2:21][N:14]([CH2:19][CH2:18]3)[CH2:15]2)[C:10]2[O:9][CH:8]=[CH:7][C:6]=2[CH:5]=1)([O-:13])=[O:12]

Participants

6

Reactant 3

HCID 13181,10-PhenanthrolineHCID 15381(+-)-3-QuinuclidinolHCID 21864764HCID 21864764, compound

Product 1

HCID 66893251HCID 66893251, compoundYield 100%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
140 °C

Procedure

7-Iodo-5-nitro-1-benzofuran (1.00 g, 3.46 mmol), quinuclidin-3-ol (1.10 g, 8.65 mmol), 1,10-phenanthroline (0.25 g, 1.38 mmol), CuI (0.13 g, 0.69 mmol) and toluene (20 mL) were mixed together and heated at 140° C. overnight. The solvent was removed in vacuo and the crude product was purified by flash chromatography (eluent: hexane and chloroform:MeOH:triethylamine; 9:0.9:0.1) to give 3-[(5-nitro-1-benzofuran-7-yl)oxy]quinuclidine (3.46 mmol).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe crude product was purified by flash chromatography (eluent: hexane and chloroform:MeOH:triethylamine; 9:0.9:0.1)

Sources & evidence

ORD record
ord-d4f1009bba4749489248532117fc2175
Source dataset
uspto-grants-2010_10
Patent number
US07820675B2

Reaction notes

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