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

HRID 641202Notes

Reaction equation

HRID 641202 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].[N:26]1([C:32]2[O:33][C:34]3[C:42](OS(C(F)(F)F)(=O)=O)=[CH:41][CH:40]=[CH:39][C:35]=3[C:36](=[O:38])[CH:37]=2)[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[N:26]1([C:32]2[O:33][C:34]3[C:42]([C:7]4[C:8]5[O:9][C:10]6[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=6[C:12]=5[C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=4)=[CH:41][CH:40]=[CH:39][C:35]=3[C:36](=[O:38])[CH:37]=2)[CH2:27][CH2:28][O:29][CH2:30][CH2:31]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 11603298trifluoro-methanesulfonic acid 2-morpholin-4-yl-4-oxo-4H-chromen-8-yl esterHCID 498572711-Nitro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)dibenzofuran

Product 1

HCID 587571622-Morpholin-4-yl-8-(1-nitro-dibenzofuran-4-yl)-1-benzopyran-4-oneYield 122.4%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
140 °C

Procedure

To a solution of 1-nitro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-dibenzofuran (12, 0.30 mmol, 0.10 g) in anhydrous dioxane (2 ml) was added trifluoro-methanesulfonic acid 2-morpholin-4-yl-4-oxo-4H-1-benzopyran-8-yl ester (0.24 mmol, 0.091 g, see WO 03/024949), potassium carbonate (0.6 mmol, 0.083 g) and tetrakis (triphenylphosphine) palladium (0.015 mmol, 0.018 g). The reaction vessel was sealed and heated under the influence of microwave radiation (140° C., 10 minutes, low absorption setting). Upon completion the reaction mixture was filtered through a thin pad of silica and the cake washed with CH2Cl2. The solvents were then removed in vacuo to give a light brown solid residue (0.13 g, 100%) which was used without further purification. m/z 443.4 [M+H]+ (Rt=4.76 min).

Workup

  1. customThe reaction vessel was sealed
  2. filtrationUpon completion the reaction mixture was filtered through a thin pad of silica
  3. washthe cake washed with CH2Cl2
  4. customThe solvents were then removed in vacuo

Sources & evidence

ORD record
ord-90b5023373674645ae61cf39ff88732b
Source dataset
uspto-grants-2010_04
Patent number
US07696203B2

Reaction notes

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