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Potassium Carbonate → 3-(4-Amino-2-fluorophenyl)-5-(1-methyl-1H-pyrazol-4-yl)pyridin-2-amine

HRID 1428113
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HRID 1428113 반응식
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([NH2:15])=[N:10][CH:11]=[C:12](Br)[CH:13]=2)=[C:4]([F:16])[CH:3]=1.[CH3:17][N:18]1[CH:22]=[C:21](B2OC(C)(C)C(C)(C)O2)[CH:20]=[N:19]1.C(=O)([O-])[O-].[K+].[K+].C(=O)(O)[O-].[Na+]>O1CCOCC1.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>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([NH2:15])=[N:10][CH:11]=[C:12]([C:21]3[CH:20]=[N:19][N:18]([CH3:17])[CH:22]=3)[CH:13]=2)=[C:4]([F:16])[CH:3]=1
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참가 물질

8

반응물 4

HCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 27739871-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 867000473-(4-Amino-2-fluorophenyl)-5-bromopyridin-2-amine

생성물 1

HCID 867000663-(4-Amino-2-fluorophenyl)-5-(1-methyl-1H-pyrazol-4-yl)pyridin-2-amine수율 93.6%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매
HCID 962Water용매
HCID 312751,4-Dioxane용매

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온도
100 °C

실험 절차

The compound obtained in Step 1 of Example 29 (2 g), 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (1.62 g), tetrakis(triphenylphosphine)palladium (0.41 g) and potassium carbonate (2.94 g) were suspended in dioxane (10 ml) and water (1 ml), and the suspension was heated under reflux at 100° C. for 61 hours. After leaving to cool, a saturated aqueous sodium bicarbonate solution was added, and the organic layer was extracted with ethyl acetate and dried over sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography [ethyl acetate:methanol=10:1 (v/v)] to give 1.88 g of the title compound as a solid.

후처리

  1. customAfter leaving
  2. temperatureto cool
  3. extractionthe organic layer was extracted with ethyl acetate
  4. dry with materialdried over sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe residue was purified by silica gel column chromatography [ethyl acetate:methanol=10:1 (v/v)]

출처 및 근거

ORD 기록
ord-6a3901e1b5454e9eaf582417589f766f
출처 데이터셋
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08933103B2

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