Potassium Fluoride → 4-methyl-3-[4-(3-methyl-3H-imidazol-4-yl)-pyrazol-1-yl]-benzoic acid ethyl ester

HRID 491852노트

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HRID 491852 반응식
[CH2:1]([O:3][C:4](=[O:18])[C:5]1[CH:10]=[CH:9][C:8]([CH3:11])=[C:7]([N:12]2[CH:16]=[C:15](Br)[CH:14]=[N:13]2)[CH:6]=1)[CH3:2].[CH3:19][N:20]1[C:24]([Sn](CCCC)(CCCC)CCCC)=[CH:23][N:22]=[CH:21]1.[F-].[K+]>O1CCOCC1.CCOC(C)=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:1]([O:3][C:4](=[O:18])[C:5]1[CH:10]=[CH:9][C:8]([CH3:11])=[C:7]([N:12]2[CH:16]=[C:15]([C:24]3[N:20]([CH3:19])[CH:21]=[N:22][CH:23]=3)[CH:14]=[N:13]2)[CH:6]=1)[CH3:2]

참가 물질

7

반응물 3

HCID 522689Potassium FluorideHCID 109156511-Methyl-5-(tri-n-butylstannyl)imidazoleHCID 588614423-(4-Bromo-pyrazol-1-yl)-4-methyl-benzoic acid ethyl ester

생성물 1

HCID 588612804-methyl-3-[4-(3-methyl-3H-imidazol-4-yl)-pyrazol-1-yl]-benzoic acid ethyl ester수율 26.5%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 8857Ethyl Acetate용매HCID 312751,4-Dioxane용매2회

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온도
100 °C

실험 절차

3-(4-Bromo-pyrazol-1-yl)-4-methyl-benzoic acid ethyl ester (Example 8) (366 mg, 1.18 mmol) was dissolved in dioxane (2 mL) and flushed with nitrogen. 1-Methyl-5-tributylstannanyl-1H-imidazole (366 mg, 0.986 mmol) was added to the reaction flask in dioxane (0.5 mL) then the flask was purged with N2. After Pd(PPh3)4 (85 mg, 0.074 mmol) was added, the reaction was heated to 100° C. in a sealed tube. The reaction mixture was stirred with a 10% KF solution for 30 min then diluted with EtOAc. The layers were separated and the aqueous layer extracted with EtOAc (3×). The organic layers were combined, dried over Na2SO4, and concentrated. The resulting residue was purified by chromatography on silica gel (5% MeOH/CH2Cl2) to give the title compound (81 mg, 22%) as a colorless oil.

후처리

  1. customflushed with nitrogen
  2. customthe flask was purged with N2
  3. customThe layers were separated
  4. extractionthe aqueous layer extracted with EtOAc (3×)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customThe resulting residue was purified by chromatography on silica gel (5% MeOH/CH2Cl2)

출처 및 근거

ORD 기록
ord-35e0271abd374558a43a1a9882a4d669
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07531560B2

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