Dimethylformamide → HCID 57671774, compound

HRID 1038492Notes

Reaction equation

HRID 1038492 reaction equation
CC1(C)COB([C:8]2[C:17]([CH2:18][O:19][C:20]3[CH:25]=[C:24]([F:26])[CH:23]=[CH:22][C:21]=3[CH3:27])=[C:16]3[C:11]([NH:12][C:13]([CH3:31])([CH3:30])[C:14](=[O:29])[N:15]3[CH3:28])=[CH:10][CH:9]=2)OC1.[N+:33]([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=1I)([O-:35])=[O:34].C(=O)([O-])O.[Na+].CN(C)C=O>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.O.C(OCC)(=O)C>[F:26][C:24]1[CH:23]=[CH:22][C:21]([CH3:27])=[C:20]([CH:25]=1)[O:19][CH2:18][C:17]1[C:8]([C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][C:36]=2[N+:33]([O-:35])=[O:34])=[CH:9][CH:10]=[C:11]2[C:16]=1[N:15]([CH3:28])[C:14](=[O:29])[C:13]([CH3:31])([CH3:30])[NH:12]2

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 69115o-IodonitrobenzeneHCID 516892Sodium BicarbonateHCID 57671777HCID 57671777, compound

Product 1

HCID 57671774HCID 57671774, compoundYield 61.1%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 7-(5,5-dimethyl[1,3,2]dioxaborinan-2-yl)-8-(5-fluoro-2-methylphenoxymethyl)-1,3,3-trimethyl-3,4-dihydro-1H-quinoxalin-2-one (Reference Compound No. 21, 68.2 mg, 0.155 mmol), 2-nitro-1-iodobenzene (79.0 mg, 0.317 mmol), sodium hydrogen carbonate (41.5 mg, 0.494 mmol) and tetrakis(triphenylphosphine)palladium (0) (19.0 mg, 0.0164 mmol) was suspended in mixed solvent of anhydrous N,N-dimethylformamide (0.5 ml) and water (0.5 mL), and stirred at 120° C. for 30 minutes by irradiated microwave. After cooling down, ethyl acetate (15 mL) and water (15 mL) were added and partitioned. The organic layer was washed with saturated brine (15 mL), dried over anhydrous magnesium sulfate, and then the solvent was removed under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate) to give the titled compound (42.6 mg) as a yellow solid. (Yield 61%)

Workup

  1. customby irradiated microwave
  2. temperatureAfter cooling down
  3. custompartitioned
  4. washThe organic layer was washed with saturated brine (15 mL)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was removed under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-1dc455e752c44166855c53ca9ed6c155
Source dataset
uspto-grants-2013_10
Patent number
US08551991B2

Reaction notes

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