Nitrogen → 6-(4-(1-(4,5-dihydrooxazol-2-yl)cyclopropyl)phenyl)-1-(4-methoxyphenyl)-3-(trifluoromethyl)-5,6-dihydro-1H-pyrazolo[3,4-c]pyridin-7(4H)-one

HRID 971152Notes

Reaction equation

HRID 971152 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:13]3[C:14](=[O:18])[NH:15][CH2:16][CH2:17][C:12]=3[C:11]([C:19]([F:22])([F:21])[F:20])=[N:10]2)=[CH:5][CH:4]=1.C(=O)([O-])[O-].[K+].[K+].N1[C:42]2[C:33](=[CH:34][CH:35]=[C:36]3[C:41]=2N=[CH:39][CH:38]=[CH:37]3)C=CC=1.[N:43]#N.[CH3:45][CH2:46][O:47][C:48](C)=O>CS(C)=O.[Cu](I)I>[O:47]1[CH2:46][CH2:45][N:43]=[C:48]1[C:37]1([C:36]2[CH:35]=[CH:34][C:33]([N:15]3[CH2:16][CH2:17][C:12]4[C:11]([C:19]([F:22])([F:20])[F:21])=[N:10][N:9]([C:6]5[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=5)[C:13]=4[C:14]3=[O:18])=[CH:42][CH:41]=2)[CH2:38][CH2:39]1

Participants

8

Reactant 5

HCID 947NitrogenHCID 13181,10-PhenanthrolineHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 218914731-(4-Methoxy-phenyl)-3-trifluoromethyl-1,4,5,6-tetrahydro-pyrazolo[3,4-c]pyridin-7-one

Product 1

HCID 103685536-(4-(1-(4,5-dihydrooxazol-2-yl)cyclopropyl)phenyl)-1-(4-methoxyphenyl)-3-(trifluoromethyl)-5,6-dihydro-1H-pyrazolo[3,4-c]pyridin-7(4H)-one

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 679Dimethyl SulfoxideSolvent

Procedure

Part B. The product from Part A (75.2 mg, 0.240 mmol) and 1-(4-methoxyphenyl)-3-(trifluoromethyl)-1,4,5,6-tetrahydro-7H-pyrazolo[3,4-c]pyridin-7-one (76.8 mg, 0.247 mmol) were dissolved in DMSO (0.5 mL). Potassium carbonate (0.109 g, 0.788 mmol), copper iodide (spatula tip), and 1,10-phenanthroline (spatula tip) were added and the reaction was heated to 120° C. for 12 h under an environment of N2. The reaction was cooled, diluted with EtOAc, washed with H2O (2×), brine, dried over Na2SO4, filtered, and concentrated in vacuo. Flash chromatography (silica, 100% EtOAc) afforded the title compound. LC/MS (ESI+) 497.6 (M+H), tR=2.44 min (10–90% CH3CN/H2O in a 4-min run). 1H NMR ((CD3)2CO, 300 MHz) δ 7.51 (d, J=9.0 Hz, 2H), 7.32 (AA′BB′, J=8.4 Hz, 4H), 6.97 (d, J=9.0 Hz, 2H), 4.16 (m, 4H), 3.82 (s, 3H), 3.67 (t, J=9.2 Hz, 2H), 3.17 (t, J=6.6 Hz, 2H), 2.02 (m, 2H), 1.42 (m, 2H), 1.17 (m, 2H) ppm.

Workup

  1. temperatureThe reaction was cooled
  2. washwashed with H2O (2×), brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1c6efc68257a49afbe8ffd66ddaef6ac
Source dataset
uspto-grants-2007_12
Patent number
US07312214B2

Reaction notes

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