Sodium Carbonate → HCID 86723264, 화합물

HRID 1846042노트

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HRID 1846042 반응식
[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

참가 물질

7

반응물 3

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

생성물 1

HCID 86723264HCID 86723264, 화합물수율 90%

시약·촉매·용매 3

HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 962Water용매HCID 312751,4-Dioxane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-7ba6c8a2a0f04c3eabbadeee4725166b
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08952008B2

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