Sodium Carbonate → HCID 19045053, compound

HRID 1781240Notes

Reaction equation

HRID 1781240 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH3:16])[CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([O:12][CH:13]([F:15])[F:14])[CH:8]=[N:7]2.[F:17][C:18]1([F:30])[O:22][C:21]2[CH:23]=[CH:24][CH:25]=[C:26](B(O)O)[C:20]=2[O:19]1.C(=O)([O-])[O-].[Na+].[Na+].C(OCC)(=O)C.CCCCCC>COCCOC.O.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[F:30][C:18]1([F:17])[O:19][C:20]2[CH:26]=[CH:25][CH:24]=[C:23]([C:2]3[CH:3]=[C:4]([CH3:16])[CH:5]=[C:6]4[C:11]=3[N:10]=[C:9]([O:12][CH:13]([F:15])[F:14])[CH:8]=[N:7]4)[C:21]=2[O:22]1

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 152390158-Bromo-2-(difluoromethoxy)-6-methylquinoxalineHCID 16427145(2,2-Difluoro-1,3-dioxaindan-4-yl)boronic acidHCID 21226206Ethyl acetate hexane

Product 1

HCID 19045053HCID 19045053, compound

Reagents, catalysts & solvents 3

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 962WaterSolvent2×HCID 80711,2-DimethoxyethaneSolvent

Procedure

To a solution of the title compound of Step E (1.65 g, 5.73 mmol) in ethylene glycol dimethyl ether (25 mL) was added the title compound of Step F (1.73 g, 8.59 mmol), a solution of sodium carbonate (1.82 g, 17.2 mmol) in water (15 mL) and bis(triphenylphosphine) palladium (II) chloride (201 mg, 0.286 mmol). The mixture was heated at reflux overnight, then cooled to room temperature and poured into water. The mixture was extracted twice with ethyl acetate. The combined organic extracts were dried (MgSO4), filtered, and concentrated under reduced pressure to give a dark-brown oil. Flash chromatography of this oil on silica gel eluting with 1:25 ethyl acetate/hexane afforded the title compound of Step G, a compound of the invention, as light-yellow solid melting at 154°-155° C. (525 mg, 25%). 1H NMR (CDCl3): δ2.64 (s,3H), 7.15-7.25 (m,3H), 7.39 (t, 1H), 7.7 (s, 1H), 7.97 (s, 1H), 8.62 (s, 1H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux overnight
  3. extractionThe mixture was extracted twice with ethyl acetate
  4. dry with materialThe combined organic extracts were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto give a dark-brown oil

Sources & evidence

ORD record
ord-6bdd1d1e091c4828a49bbd517c400336
Source dataset
uspto-grants-1997_05
Patent number
US05633218

Reaction notes

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