Hydrochloric Acid → HCID 118557958, compound

HRID 2207193Notes

Reaction equation

HRID 2207193 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1/[CH:8]=[C:9]1/[C:10](=[O:22])[C:11]2[C:16]([CH2:17]/1)=[CH:15][C:14]([O:18][CH3:19])=[C:13]([O:20][CH3:21])[CH:12]=2.[CH2:23]([O:25]C([Sn](CCCC)(CCCC)CCCC)=C)[CH3:24].Cl>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:23]([C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1/[CH:8]=[C:9]1/[C:10](=[O:22])[C:11]2[C:16]([CH2:17]/1)=[CH:15][C:14]([O:18][CH3:19])=[C:13]([O:20][CH3:21])[CH:12]=2)(=[O:25])[CH3:24]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 118558042HCID 118558042, compound

Product 1

HCID 118557958HCID 118557958, compoundYield 81%

Reagents, catalysts & solvents 3

HCID 11776TriphenylphosphineCatalystHCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumCatalystHCID 1140TolueneSolvent2×

Conditions

Temperature
110 °C

Procedure

A toluene solution (3 mL) of compound 89 (0.4 g, 1.1 mmol), Pd(dba)2 (25.3 mg, 0.044 mmol) and PPh3 (23.1 mg, 0.088 mmol) was stirred at room temperature under argon for 15 min. Then, (1-ethoxyvinyl)tri(n-butyl)stannane (0.38 mL, 1.1 mmol) in toluene (3 mL) was added and the resulting mixture was stirred overnight at 110° C., cooled to room temperature and filtered on Celite, washed with EtOAc and concentrated under reduced pressure. Purification on silica gel (gradient of EtOAc in Petroleum ether) afford the product which was placed in presence of an aqueous solution of HCl 1M for 30 minutes at room temperature. After neutralization with a saturated aqueous solution of NaHCO3, aqueous phase was extracted with dichloromethane and the combined organic layers were dried over magnesium sulfate to afford the title compound 97 (Yield 288.1 mg, 81%) which was used without further purification.

Workup

  1. temperaturecooled to room temperature
  2. filtrationfiltered on Celite
  3. washwashed with EtOAc
  4. concentrationconcentrated under reduced pressure
  5. customPurification on silica gel (gradient of EtOAc in Petroleum ether)
  6. customafford the product which
  7. extractionAfter neutralization with a saturated aqueous solution of NaHCO3, aqueous phase was extracted with dichloromethane
  8. dry with materialthe combined organic layers were dried over magnesium sulfate

Sources & evidence

ORD record
ord-02f35757922f4044bc68eb9d6b31c0c4
Source dataset
uspto-grants-2016_06
Patent number
US09376387B2

Reaction notes

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