Triethylamine → HCID 18398676, compound

HRID 1018961Notes

Reaction equation

HRID 1018961 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([Br:12])[CH:11]=1)[N:8]=[C:7]([CH3:13])[CH:6]=[CH:5]2.[CH2:14]([O:16][P:17]([O-:21])[O:18][CH2:19][CH3:20])[CH3:15].CCN(CC)CC.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C1(C)C=CC=CC=1.CCOC(C)=O.CC([O-])=O.CC([O-])=O.[Pd+2]>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([P:17](=[O:21])([O:18][CH2:19][CH3:20])[O:16][CH2:14][CH3:15])[CH:11]=1)[N:8]=[C:7]([CH3:13])[CH:6]=[CH:5]2.[Br:12][C:10]1[CH:11]=[C:2]([P:17](=[O:21])([O:18][CH2:19][CH3:20])[O:16][CH2:14][CH3:15])[CH:3]=[C:4]2[C:9]=1[N:8]=[C:7]([CH3:13])[CH:6]=[CH:5]2

Participants

9

Reactant 4

HCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 3780918DiethylphosphiteHCID 18374503HCID 18374503, compound

Product 2

HCID 18398676HCID 18398676, compoundYield 13%HCID 18398690HCID 18398690, compoundYield 4%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

To a degassed solution of 6,8-dibromo-2-methylquinoline (3.01 g, 10 mmol, prepared according to Song et al. J. Heterocyclic Chem. 1993, 39, 17.), diethylphosphite (1.65 g, 12 mmol) and Et3N (1.21 g, 12 mmol) in toluene (3 mL) was added Pd(OAc)2 (224.5 mg, 1 mmol). The mixture was degassed and Ph3P (1.049 g, 4 mmol) was added. The mixture was heated to 100° C. for 7 h, cooled, diluted with EtOAc (200 mL) and filtered through celite. The filtrate was concentrated in vacuo. The residue was purified by chromatography on silica gel to give 475 mg (13%) of diethyl 6-bromo-2-methyl-8-quinolylphosphonate and 150 mg (4%) of diethyl 8-bromo-2-methyl-6-quinolylphosphonate.

Workup

  1. customThe mixture was degassed
  2. temperaturecooled
  3. filtrationfiltered through celite
  4. concentrationThe filtrate was concentrated in vacuo
  5. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-8b5a5ab77b6449e1a26b9954b91c07ca
Source dataset
uspto-grants-2002_11
Patent number
US06486141B2

Reaction notes

Loading…