Potassium Carbonate → 2-Morpholin-4-yl-8-(1-nitro-dibenzofuran-4-yl)-1H-quinolin-4-one

HRID 641201Notes

Reaction equation

HRID 641201 reaction equation
[N+:1]([C:4]1[C:12]2[C:11]3[CH:13]=[CH:14][CH:15]=[CH:16][C:10]=3[O:9][C:8]=2[C:7](B2OC(C)(C)C(C)(C)O2)=[CH:6][CH:5]=1)([O-:3])=[O:2].C(=O)([O-])[O-].[K+].[K+].Br[C:33]1[CH:34]=[CH:35][CH:36]=[C:37]2[C:42]=1[NH:41][C:40]([N:43]1[CH2:48][CH2:47][O:46][CH2:45][CH2:44]1)=[CH:39][C:38]2=[O:49]>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[N:43]1([C:40]2[NH:41][C:42]3[C:37]([C:38](=[O:49])[CH:39]=2)=[CH:36][CH:35]=[CH:34][C:33]=3[C:7]2[C:8]3[O:9][C:10]4[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=4[C:12]=3[C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)[CH2:44][CH2:45][O:46][CH2:47][CH2:48]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 177584828-bromo-2-morpholin-4-yl-1H-quinolin-4-oneHCID 498572711-Nitro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)dibenzofuran

Product 1

HCID 498574722-Morpholin-4-yl-8-(1-nitro-dibenzofuran-4-yl)-1H-quinolin-4-oneYield 60.2%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent2×

Procedure

In a Schlenk tube, 1-nitro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) dibenzofuran (12) (500 mg, 1.47 mmol) and potassium carbonate (480 mg, 3.69 mmol) were solubilised in dioxane (10 mL) and degassed. Concurrently, 8-bromo-2-morpholin-4-yl-1H-quinolin-4-one (21) (380 mg, 1.23 mmol) and Pd(PPh3)4 (71 mg, 0.06 mmol) were solubilised in dioxane (10 mL) and degassed. The solutions were mixed together in a microwave vessel, which was placed into the microwave reactor at 180° C. for 30 min. Upon cooling, DCM (20 mL) was added. The solution was washed with water (20 mL), then dried on magnesium sulfate and evaporated. The residue was purified by flash chromatography using AcOEt/EP (8:2) as eluant to furnish the title compound (303 mg, 0.74 mmol, 60%) as a yellow solid: Rf=0.67 (AcOEt); mp: 247° C.; λmax (EtOH)/nm 251; IR (cm−1) 3421, 2852, 2360, 2333, 1614, 1573, 1500, 1435, 1429, 1348, 1309, 1233, 1199, 1152, 1124, 1039, 991, 917, 866, 823; 1H NMR, (300 MHz, CDCl3) δ 3.04 (4H, m, 2×CH2—N-morpholine), 3.54 (4H, m, 2×CH2—O-morpholine), 5.92 (1H, s, H-3), 7.19-7.45 (2H, m), 7.51-7.58 (2H, m), 7.65-7.70 (2H, m), 8.31 (2H, m), 8.67 (1H, d, J=7 Hz); MS (EI) m/z 442.29 M+; HRMS calcd for C25H20N3O5 [M+H]+ 442.1397, found 442.1398.

Workup

  1. customdegassed
  2. customdegassed
  3. additionThe solutions were mixed together in a microwave vessel
  4. temperatureUpon cooling
  5. additionDCM (20 mL) was added
  6. washThe solution was washed with water (20 mL)
  7. customdried on magnesium sulfate
  8. customevaporated
  9. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-756e16427c0743e5a850d5f8215ca145
Source dataset
uspto-grants-2010_04
Patent number
US07696203B2

Reaction notes

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