HCID 10982303, compound → HCID 10050391, compound

HRID 457579Notes

Reaction equation

HRID 457579 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]2[O:12][C:11]([NH:13][C:14]3[CH:19]=[C:18]([S:20]([CH2:23][CH3:24])(=[O:22])=[O:21])[CH:17]=[CH:16][C:15]=3[O:25][CH3:26])=[N:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.[F:27][C:28]1[CH:29]=[C:30]([Sn](CCCC)(CCCC)CCCC)[CH:31]=[C:32]([F:34])[CH:33]=1>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.C(#N)C.C(OCC)(=O)C>[F:27][C:28]1[CH:29]=[C:30]([C:2]2[CH:7]=[CH:6][CH:5]=[C:4]([C:8]3[O:12][C:11]([NH:13][C:14]4[CH:19]=[C:18]([S:20]([CH2:23][CH3:24])(=[O:21])=[O:22])[CH:17]=[CH:16][C:15]=4[O:25][CH3:26])=[N:10][CH:9]=3)[CH:3]=2)[CH:31]=[C:32]([F:34])[CH:33]=1

Participants

6

Reactant 2

HCID 10982303HCID 10982303, compoundHCID 11487418HCID 11487418, compound

Product 1

HCID 10050391HCID 10050391, compoundYield 63%

Reagents, catalysts & solvents 3

HCID 70681Tetrabutylammonium ChlorideCatalystHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

In a pyrex sealed tube, a mixture of the title compound of Example 100 (123 mg, 0.28 mmol), 3,5-difluoro(tributylstannyl)benzene (400 mg, 1 mmol), tetrabutylammonium chloride (170 mg, 0.61 mmol), and tetrakistriphenylphosphine palladium(0) (20 mg, 0.017 mmol) was suspended in dry acetonitrile (10 mL) and stirred at 100° C. After the reaction was determine to be complete by TLC analysis, the reaction was cooled and diluted with ethyl acetate (50 mL), quenched with 1M aqueous potassium fluoride solution (20 mL), and stirred for 3 h. The organic layer was separated, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel eluting with hexane:ethyl acetate (1:1) to afford the title compound (83 mg, 63%) as a solid white powder. 1H NMR (400 MHz, d6-DMSO): δ 9.72 (s, 1H), 8.74 (d, J=2.2, 1H), 7.91 (s, 1H), 7.60–7.64 (m, 3H), 7.42–7.53 (m, 4H), 7.23 (d, J=8.6, 1H), 3.94 (s, 3H), 3.16 (q, J=7.3, 2H), 1.07 (t, J=7.3, 3H). MS (ES+, m/z)=471 (m+H)+.

Workup

  1. customIn a pyrex sealed tube
  2. temperaturethe reaction was cooled
  3. customquenched with 1M aqueous potassium fluoride solution (20 mL)
  4. stirringstirred for 3 h
  5. customThe organic layer was separated
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe crude product was purified by column chromatography on silica gel eluting with hexane:ethyl acetate (1:1)

Sources & evidence

ORD record
ord-2ff379cd5c274954a0366824792d0683
Source dataset
uspto-grants-2007_03
Patent number
US07189712B2

Reaction notes

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