Hydrochloric Acid → HCID 57883105, compound

HRID 1817784Notes

Reaction equation

HRID 1817784 reaction equation
Br[C:2]1[C:11]2[O:10][C:9]([C:12]3[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=3)=[CH:8][C:7](=[O:18])[C:6]=2[CH:5]=[C:4]([CH3:19])[CH:3]=1.[CH:20]([O:22]CCCC)=[CH2:21].C(N(CC)CC)C.Cl>CN(C=O)C.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:19][C:4]1[CH:3]=[C:2]([C:20](=[O:22])[CH3:21])[C:11]2[O:10][C:9]([C:12]3[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=3)=[CH:8][C:7](=[O:18])[C:6]=2[CH:5]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 8108Butyl vinyl etherHCID 8471TriethylamineHCID 57883111HCID 57883111, compound

Product 1

HCID 57883105HCID 57883105, compoundYield 2.5%

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 8-bromo-2-(4-pyridinyl)-6-methyl-4H-1-benzopyran-4-one (0.12 g, 0.36 mmol), n-butyl vinyl ether (0.047 ml, 0.36 mmol), triethylamine (0.050 ml, 0.36 mmol) in DMF (5 ml) was purged with N2 and then treated with PdCl2(dppf) (27 mg, 0.036 mmol). The mixture was heated to 90° C. overnight. The mixture was cooled to room temperature and treated with 1N aqueous HCl (30 ml) and stirring was continued overnight. The mixture was then diluted with water (50 ml), and lyophilized to dryness. The residue was eluted through a C8-HPLC column and the product isolated as an off-white solid (2.5 mg). The product was identical to that described above.

Workup

  1. customwas purged with N2
  2. temperatureThe mixture was cooled to room temperature
  3. washThe residue was eluted through a C8-HPLC column

Sources & evidence

ORD record
ord-e80e27fc9ce94fffbc20e9f8ca948a20
Source dataset
uspto-grants-2009_10
Patent number
US07598377B2

Reaction notes

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