Dimethylformamide → HCID 57671774, compound

HRID 871989Notes

Reaction equation

HRID 871989 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-863029a75ee143378e0121f31314986d
Source dataset
uspto-grants-2015_03
Patent number
US08975256B2

Reaction notes

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