Dichloromethane → tert-butyl 4-(5-chloro-2-hydroxyphenyl)-1H-pyrazole-1-carboxylate

HRID 46295

반응식

HRID 46295 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4](I)[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].CC1(C)C(C)(C)OB([C:24]2[CH:25]=[N:26][N:27]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH:28]=2)O1.ClCCl>O1CCOCC1.O.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.[Pd]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([C:24]2[CH:25]=[N:26][N:27]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH:28]=2)[CH:3]=1

참가 물질

8

반응물 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 6202344-Chloro-2-iodophenolHCID 16217654tert-butyl 4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-1-carboxylate

생성물 1

HCID 59436518tert-butyl 4-(5-chloro-2-hydroxyphenyl)-1H-pyrazole-1-carboxylate수율 66%

시약·촉매·용매 3

HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 962Water용매2회HCID 312751,4-Dioxane용매

반응 조건

온도
50 °C

실험 절차

A suspension of 4-chloro-2-iodophenol (200 mg, 0.78 mmol) and potassium carbonate (434 mg, 3.14 mmol) in 1,4-dioxane (3 mL) and water (1 mL) was degassed and heated for 1 hour at 50° C. tert-Butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-1-carboxylate (347 mg, 1.18 mmol) and palladium (0) tetrakis(triphenylphoshine) (91 mg, 0.08 mmol) were added and the mixture heated at 50° C. for 5 hours. Dichloromethane (20 ml) and water (10 ml) were added and the organics separated and evaporated in vacuo. The residue was purified by column chromatography (silica gel) eluting with ethyl acetate:heptane (2:8 to 1:0, by volume) to afford the title product as a white solid, 155 mg, 66% yield.

후처리

  1. customwas degassed
  2. additionwere added
  3. customthe organics separated
  4. customevaporated in vacuo
  5. customThe residue was purified by column chromatography (silica gel)
  6. washeluting with ethyl acetate:heptane (2:8 to 1:0, by volume)

출처 및 근거

ORD 기록
ord-49e6dad53c78479fad1a4142b9f5c63e
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08541588B2

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