Hydrochloric Acid → HCID 57883105, compound

HRID 253041Notes

Reaction equation

HRID 253041 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-25a1af58c1c349f7a2000bfa113b7cf6
Source dataset
uspto-grants-2011_01
Patent number
US07872011B2

Reaction notes

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