Potassium Carbonate → 2-{[5-amino-1-methyl-4-(4-methylphenyl)-1H-pyrazol-3-yl]oxy}ethyl acetate

HRID 1062780

반응식

HRID 1062780 반응식
[NH2:1][C:2]1[N:6]([CH3:7])[N:5]=[C:4]([OH:8])[C:3]=1[C:9]1[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=1.C(=O)([O-])[O-].[K+].[K+].[C:22]([O:25][CH2:26][CH2:27]Br)(=[O:24])[CH3:23]>CN(C)C=O.O>[C:22]([O:25][CH2:26][CH2:27][O:8][C:4]1[C:3]([C:9]2[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=2)=[C:2]([NH2:1])[N:6]([CH3:7])[N:5]=1)(=[O:24])[CH3:23]

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 135641-Acetoxy-2-bromoethaneHCID 1784239155-amino-1-methyl-4-(4-methylphenyl)-1H-pyrazol-3-ol

생성물 1

HCID 222820022-{[5-amino-1-methyl-4-(4-methylphenyl)-1H-pyrazol-3-yl]oxy}ethyl acetate수율 42.5%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

To 5-amino-1-methyl-4-(4-methylphenyl)-1H-pyrazol-3-ol (Preparation 3a) (250 mg) in dimethyl formamide (5 ml) at room temperature was added potassium carbonate (510 mg) and 2-bromoethyl acetate (205 mg), the mixture was stirred for 16 hrs. The reaction was diluted with water (60 ml) and extracted with ethyl acetate (3×30 ml). The organic fractions were combined, washed with water (2×30 ml) and brine (30 ml) and dried over magnesium sulfate, filtered concentrated under reduced pressure. The residue was purified by column chromatography (silica, 30 g) eluted with ethyl acetate:hexane (1:1) to yield the title compound as a white solid (151 mg).

후처리

  1. extractionextracted with ethyl acetate (3×30 ml)
  2. washwashed with water (2×30 ml) and brine (30 ml)
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography (silica, 30 g)
  7. washeluted with ethyl acetate:hexane (1:1)

출처 및 근거

ORD 기록
ord-7c6011bb5ebc44cfac5fedd349445810
출처 데이터셋
uspto-grants-2005_11
특허 번호
US06962923B2

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