1,10-Phenanthroline → HCID 90386964, compound

HRID 2170204Notes

Reaction equation

HRID 2170204 reaction equation
[CH3:1][C:2]1[N:3]([CH2:28][O:29][CH2:30][CH2:31][Si:32]([CH3:35])([CH3:34])[CH3:33])[C:4]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[O:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[C:5]2[CH:10]=[C:9](C(O)=O)[NH:8][C:7](=[O:14])[C:6]=12.N1C2C(=CC=C3C=2N=CC=C3)C=CC=1>CN1CCCC1=O.N1C2C(=CC=CC=2)C=CC=1.[Cu-]=O>[CH3:1][C:2]1[N:3]([CH2:28][O:29][CH2:30][CH2:31][Si:32]([CH3:33])([CH3:35])[CH3:34])[C:4]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[O:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[C:5]2[CH:10]=[CH:9][NH:8][C:7](=[O:14])[C:6]=12

Participants

6

Reactant 2

HCID 13181,10-PhenanthrolineHCID 90387127HCID 90387127, compound

Product 1

HCID 90386964HCID 90386964, compound

Reagents, catalysts & solvents 3

HCID 178419072HCID 178419072, compoundCatalystHCID 7047QuinolineSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
190 °C

Procedure

To a solution of Example 12a (0.037 g, 0.075 mmol) in a mixture of N-methyl-2-pyrrolidinone (0.3 mL) and quinoline (0.100 mL) were added 1,10-phenanthroline (0.027 g, 0.15 mmol) and copper(I) oxide (0.01 g, 0.075 mmol). The mixture sparged with nitrogen for 30 minutes and heated in a Biotage microwave reactor at 190° C. for 1 hour. The reaction mixture was partitioned between ethyl acetate and water, washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, filtered and concentrated to afford a mixture of products containing the title compound.

Workup

  1. customThe mixture sparged with nitrogen for 30 minutes
  2. customThe reaction mixture was partitioned between ethyl acetate and water
  3. washwashed with saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto afford
  8. additiona mixture of products

Sources & evidence

ORD record
ord-d2a4ff8689144b7399953b239e3cff4a
Source dataset
uspto-grants-2015_06
Patent number
US09050346B2

Reaction notes

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