1,10-Phenanthroline → HCID 136350250, compound

HRID 1410175Notes

Reaction equation

HRID 1410175 reaction equation
[CH:1]([C:3]1[N:7]([CH3:8])[N:6]=[C:5]([C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)[C:4]=1[C:16]1[C:17]([CH3:25])=[C:18](C(O)=O)[O:19][C:20]=1[CH3:21])=[O:2].N1C2C(=CC=C3C=2N=CC=C3)C=CC=1>N1C2C(=CC=CC=2)C=CC=1.CN1C(=O)CCC1>[CH3:21][C:20]1[O:19][CH:18]=[C:17]([CH3:25])[C:16]=1[C:4]1[C:5]([C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)=[N:6][N:7]([CH3:8])[C:3]=1[CH:1]=[O:2]

Participants

5

Reactant 2

HCID 13181,10-PhenanthrolineHCID 136350249HCID 136350249, compound

Product 1

HCID 136350250HCID 136350250, compoundYield 51.9%

Reagents, catalysts & solvents 2

HCID 7047QuinolineSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A mixture of 4-(5-formyl-3-(4-hydroxyphenyl)-1-methyl-1H-pyrazol-4-yl)-3,5-dimethylfuran-2-carboxylic acid (45 mg, 0.13 mmol), phenantroline (9.53 mg, 0.05 mmol) and Cu2O (3.78 mg, 0.026 mmol) in quinoline (0.73 ml) and NMP (2.19 mL) was flushed with N2 and irradiated in the microwave at 190° C. for 15 min. HCl (1M) and CH2Cl2 were added and the phases were separated. The crude product was purified on preparative IIPLC to give 4-(2,4-dimethylfuran-3-yl)-3-(4-hydroxyphenyl)-1-methyl-1H-pyrazole-5-carbaldehyde (20.0 mg, 51%).

Workup

  1. customwas flushed with N2
  2. customirradiated in the microwave at 190° C. for 15 min
  3. additionHCl (1M) and CH2Cl2 were added
  4. customthe phases were separated
  5. customThe crude product was purified on preparative IIPLC

Sources & evidence

ORD record
ord-dbce0bb529cb46319ab1ef452e5fcf2f
Source dataset
uspto-grants-2014_12
Patent number
US08921402B2

Reaction notes

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