Sodium Bicarbonate → HCID 89666712, compound

HRID 2171261Notes

Reaction equation

HRID 2171261 reaction equation
C([Sn](CCCC)(CCCC)[C:6]([O:8]CC)=[CH2:7])CCC.Br[C:20]1[C:21]([O:29][CH3:30])=[N:22][CH:23]=[C:24]([N+:26]([O-:28])=[O:27])[CH:25]=1.C(=O)([O-])O.[Na+]>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.CC(N(C)C)=O>[CH3:30][O:29][C:21]1[C:20]([C:6](=[O:8])[CH3:7])=[CH:25][C:24]([N+:26]([O-:28])=[O:27])=[CH:23][N:22]=1

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 215844513-Bromo-2-methoxy-5-nitropyridine

Product 1

HCID 89666712HCID 89666712, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 31374DimethylacetamideSolvent

Procedure

Pd(PPh3)4 (60 mg) and tributyl (1-ethoxyvinyl)tin were added to a DMAc (3 ml) solution containing 3-bromo-2-methoxy-5-nitropyridine (69 mg) obtained in the 1st step, followed by microwave irradiation (Initiator™, 180° C., 10 minutes, 2.45 GHz, 0-240 W). Saturated sodium hydrogen carbonate was added to the reaction solution, followed by extraction with ethyl acetate. The organic layers were dried over anhydrous sodium sulfate. The solvent was distilled away under reduced pressure and the obtained residue was purified by silica gel chromatography (n-hexane:ethyl acetate=9:1 to 3:7). A light yellow solid of 1-(2-methoxy-5-nitropyridin-3-yl)ethanone (72 mg) was thus obtained.

Workup

  1. customobtained in the 1st step
  2. customfollowed by microwave irradiation (Initiator™, 180° C., 10 minutes, 2.45 GHz, 0-240 W)
  3. extractionfollowed by extraction with ethyl acetate
  4. dry with materialThe organic layers were dried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled away under reduced pressure
  6. customthe obtained residue was purified by silica gel chromatography (n-hexane:ethyl acetate=9:1 to 3:7)

Sources & evidence

ORD record
ord-2fb580608878463381dbe115811dd7c2
Source dataset
uspto-grants-2015_06
Patent number
US09051310B2

Reaction notes

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