1,10-Phenanthroline → HCID 69516007, compound

HRID 971158Notes

Reaction equation

HRID 971158 reaction equation
[C:1]([O:5][C:6](=[O:18])[NH:7][C:8]1([C:11]2[CH:16]=[CH:15][C:14](I)=[CH:13][CH:12]=2)[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[CH2:19]([O:21][C:22]([C:24]1[C:32]2[CH2:31][CH2:30][NH:29][C:28](=[O:33])[C:27]=2[N:26]([C:34]2[CH:39]=[CH:38][C:37]([O:40][CH3:41])=[CH:36][CH:35]=2)[N:25]=1)=[O:23])[CH3:20].C([O-])([O-])=O.[K+].[K+].N1C2C(=CC=C3C=2N=CC=C3)C=CC=1>CS(C)=O.[Cu]I.CCOC(C)=O>[CH2:19]([O:21][C:22]([C:24]1[C:32]2[CH2:31][CH2:30][N:29]([C:14]3[CH:15]=[CH:16][C:11]([C:8]4([NH:7][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:18])[CH2:10][CH2:9]4)=[CH:12][CH:13]=3)[C:28](=[O:33])[C:27]=2[N:26]([C:34]2[CH:35]=[CH:36][C:37]([O:40][CH3:41])=[CH:38][CH:39]=2)[N:25]=1)=[O:23])[CH3:20]

Participants

8

Reactant 4

HCID 13181,10-PhenanthrolineHCID 11430Potassium CarbonateHCID 22240468Ethyl 1-(4-methoxyphenyl)-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo(3,4-c)pyridine-3-carboxylateHCID 59019959tert-Butyl (1-(4-iodophenyl)cyclopropyl)carbamate

Product 1

HCID 69516007HCID 69516007, compoundYield 46.2%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
120 °C

Procedure

Part A. [1-(4-Iodo-phenyl)-cyclopropyl]-carbamic acid tert-butyl ester (0.34 g, 0.95 mmol) and 1-(4-methoxy-phenyl)-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxylic acid ethyl ester (0.30 g, 0.97 mmol) were stirred in DMSO (1 mL). K2CO3 (0.25 g, 1.81 mmol), CuI (87 mg, 0.46 mmol) and 1,10-phenanthroline (83 mg, 0.46 mmol) were added. The resulting mixture was heated at 120° C. for 2.5 h. After cooling, it was extracted with EtOAc (2×), washed with H2O and brine, dried over MgSO4, filtered, and concentrated to dryness. The residue was purified by FCC (silica gel, CH2Cl2:EtOAc=1:1, then EtOAc) to give 6-[4-(1-tert-butoxycarbonylamino-cyclopropyl)-phenyl]-1-(4-methoxy-phenyl)-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxylic acid ethyl ester (0.24 g, yield: 46%).

Workup

  1. temperatureAfter cooling
  2. extractionit was extracted with EtOAc (2×)
  3. washwashed with H2O and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated to dryness
  7. customThe residue was purified by FCC (silica gel, CH2Cl2

Sources & evidence

ORD record
ord-b2edc9aaa12f49dc9fbf5a3bd54c5f93
Source dataset
uspto-grants-2007_12
Patent number
US07312214B2

Reaction notes

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