Potassium Carbonate → [8-(2-chlorophenyl)-6-fluoro-2H-chromen-2-yl]methyl 4-methylbenzenesulfonate

HRID 902328

반응식

HRID 902328 반응식
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([O:11][CH2:12][CH:13]2[CH:22]=[CH:21][C:20]3[C:15](=[C:16](Br)[CH:17]=[C:18]([F:23])[CH:19]=3)[O:14]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[Cl:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1B(O)O.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.O.CC1C(P(C2C(C)=CC=CC=2)C2C(C)=CC=CC=2)=CC=CC=1.CC1C(P(C2C(C)=CC=CC=2)C2C(C)=CC=CC=2)=CC=CC=1.Cl[Pd]Cl>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([O:11][CH2:12][CH:13]2[CH:22]=[CH:21][C:20]3[C:15](=[C:16]([C:27]4[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=4[Cl:25])[CH:17]=[C:18]([F:23])[CH:19]=3)[O:14]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

참가 물질

7

반응물 3

HCID 11430Potassium CarbonateHCID 27343222-Chlorophenylboronic acidHCID 86609107(8-bromo-6-fluoro-2H-chromen-2-yl)methyl 4-methylbenzenesulfonate

생성물 1

HCID 86609118[8-(2-chlorophenyl)-6-fluoro-2H-chromen-2-yl]methyl 4-methylbenzenesulfonate수율 53%

시약·촉매·용매 3

HCID 10876480Bis(tri-o-tolylphosphine)palladium(II) Dichloride촉매HCID 962Water용매HCID 312751,4-Dioxane용매

반응 조건

온도
100 °C

실험 절차

A solution of (8-bromo-6-fluoro-2H-chromen-2-yl)methyl 4-methylbenzenesulfonate, prepared in Example 37, step 5 (1.0 g, 2.42 mmol) and 2-chlorophenylboronic acid (1.14 g, 7.26 mmol) in dioxane (18 mL) was added a solution of potassium carbonate (1.0 g, 7.26 mmol) in water (6 mL) and the mixture purged with nitrogen for 20 minutes. Trans-dichlorobis(tri-o-tolylphosphine)palladium (II) (95 mg, 0.12 mmol) was added and the reaction mixture heated at 100° C. for 2 hours. The cooled reaction mixture was then partitioned between ethyl acetate (100 mL) and 2.0 M aqueous sodium hydroxide (100 mL). The organic layer was separated, washed with water (100 mL) and saturated brine (100 mL), dried over magnesium sulfate, filtered and concentrated under reduced pressure to afford a yellow oil. Purification by flash chromatography using a solvent gradient of 5 to 20% ethyl acetate in hexane gave 0.57 g (53%) of [8-(2-chlorophenyl)-6-fluoro-2H-chromen-2-yl]methyl 4-methylbenzenesulfonate as a white solid. HRMS: calcd for C23H18ClFO4S+NH4+, 462.09366. found (ESI, [M+NH4]+), 462.0916.

후처리

  1. customthe mixture purged with nitrogen for 20 minutes
  2. customThe cooled reaction mixture
  3. customwas then partitioned between ethyl acetate (100 mL) and 2.0 M aqueous sodium hydroxide (100 mL)
  4. customThe organic layer was separated
  5. washwashed with water (100 mL) and saturated brine (100 mL)
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customto afford a yellow oil
  10. customPurification by flash chromatography

출처 및 근거

ORD 기록
ord-46abf995a311477fb67fab9f5008980a
출처 데이터셋
uspto-grants-2008_04
특허 번호
US07365095B2

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