Dimethylformamide → HCID 52914155, compound

HRID 341032Notes

Reaction equation

HRID 341032 reaction equation
[N:1]1[NH:2][C:3](=[O:14])[C:4]2[C:13]=1[C:12]1[CH:11]=[CH:10][CH:9]=[CH:8]C=1NC=2.P([O-])([O-])([O-])=O.[K+].[K+].[K+].CN[C@@H:25]1[CH2:30][CH2:29][CH2:28][CH2:27][C@H:26]1NC.[F:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=1I.[CH3:41][N:42]([CH3:45])[CH:43]=O>[Cu]I>[F:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=1[N:2]1[C:3](=[O:14])[C:4]2=[CH:41][N:42]([CH2:43][C:29]3[CH:28]=[CH:27][C:26]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)=[CH:25][CH:30]=3)[C:45]3[CH:8]=[CH:9][CH:10]=[CH:11][C:12]=3[C:13]2=[N:1]1

Participants

7

Reactant 5

HCID 6228DimethylformamideHCID 62657Potassium Phosphate, TribasicHCID 676731-Fluoro-2-iodobenzeneHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 178518774HCID 178518774, compound

Product 1

HCID 52914155HCID 52914155, compound

Reagents, catalysts & solvents 1

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Catalyst

Procedure

5-Biphenyl-4-ylmethyl)-2,5-dihydro-3H-pyrazolo[4,3-c]quinolin-3-one (51 mg, 0.14 mmol), potassium phosphate (77 mg, 0.36 mmol, 2.5 equiv), (±)-trans-N,N′-bismethyl-1,2-cyclohexane diamine (4.1 mg, 0.029 mmol, 0.2 equiv), copper(I) iodide (2.8 mg, 0.015 mmol, 0.1 equiv) and 2-fluoroiodobenzene (17 μL, 0.14 mmol, 1 equiv) were combined in a sealed tube containing N,N-dimethylformamide (2 mL). The mixture was sparged under a nitrogen atmosphere, the vessel was sealed and placed into an preheated oil bath at 110° C. for 15 hours. The mixture was cooled to ambient temperature, poured into sodium bicarbonate (20 mL, aqueous saturated) and extracted with ethyl acetate (2×75 mL). The combined organic extracts were dried with sodium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel gradient chromatography (100:0 to 95:5; dichloromethane:methanol), providing the titled compound: 1H-NMR (500 MHz, d6-DMSO) δ 9.17 (1H, s), 8.21 (1H, dd, J=8.0, 1.4 Hz), 7.80 (1H, d, J=8.6 Hz), 7.66 (2H, d, J=8.2 Hz), 7.64-7.59 (4H, m), 7.54 (1H, t, J=7.4 Hz), 7.46-7.32 (8H, m), 5.79 (2H, s) ppm; high resolution mass spectrometry (ES+) m/z 446.1668 [(M+H)+; calculated for C29H21FN3O: 446.1663].

Workup

  1. customThe mixture was sparged under a nitrogen atmosphere
  2. customthe vessel was sealed
  3. additionpoured into sodium bicarbonate (20 mL, aqueous saturated)
  4. extractionextracted with ethyl acetate (2×75 mL)
  5. dry with materialThe combined organic extracts were dried with sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by silica gel gradient chromatography (100:0 to 95:5; dichloromethane:methanol)

Sources & evidence

ORD record
ord-f2deeda54cd641149a31f836426104a9
Source dataset
uspto-grants-2014_11
Patent number
US08895580B2

Reaction notes

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