Sodium Carbonate → HCID 86723264, compound

HRID 1846042Notes

Reaction equation

HRID 1846042 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:11][CH3:12])=[C:6](B(O)O)[CH:7]=1.Br[C:14]1[CH:19]=[CH:18][C:17]([S:20]([CH2:23][CH3:24])(=[O:22])=[O:21])=[CH:16][C:15]=1[F:25].C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.O.[Pd].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.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>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:11][CH3:12])=[C:6]([C:14]2[CH:19]=[CH:18][C:17]([S:20]([CH2:23][CH3:24])(=[O:22])=[O:21])=[CH:16][C:15]=2[F:25])[CH:7]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 27357515-Chloro-2-methoxyphenylboronic acidHCID 67280287HCID 67280287, compound

Product 1

HCID 86723264HCID 86723264, compoundYield 90%

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of (5-chloro-2-methoxyphenyl)boronic acid (714 mg, 1.68 mmol) in dioxane (5 mL) and water (1 mL) was added 1-bromo-4-(ethylsulfonyl)-2-fluorobenzene (Preparation 19, 450 mg, 1.68 mmol), and sodium carbonate (534 mg, 5.04 mmol). The reaction was degassed and then tetrakis(triphenylphosphine) palladium(0) (194 mg, 0.17 mmol) was added and the reaction mixture further degassed. The reaction was placed on a preheated hot plate (110° C.) for 16 hours. The reaction mixture was cooled to room temperature and filtered through celite and the solvent removed in vacuo. The crude material was purified by silica gel column chromatography eluting with EtOAc:cyclohexane 40:60 to give the title compound as a brown oil in 90% yield, 500 mg.

Workup

  1. customThe reaction was degassed
  2. filtrationfiltered through celite
  3. customthe solvent removed in vacuo
  4. customThe crude material was purified by silica gel column chromatography
  5. washeluting with EtOAc:cyclohexane 40:60

Sources & evidence

ORD record
ord-7ba6c8a2a0f04c3eabbadeee4725166b
Source dataset
uspto-grants-2015_02
Patent number
US08952008B2

Reaction notes

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