Potassium Phosphate, Tribasic → 5-Amino-1-(4-fluorophenyl)-4-[3-(pyridin-3-yl)benzoyl]pyrazole

HRID 429356노트

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HRID 429356 반응식
[NH2:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=2)[N:5]=[CH:4][C:3]=1[C:14](=[O:22])[C:15]1[CH:20]=[CH:19][CH:18]=[C:17](Br)[CH:16]=1.[N:23]1[CH:28]=[CH:27][CH:26]=[C:25](B(O)O)[CH:24]=1.B1(C2C=CC=NC=2)OCCCO1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.[Cl-].[Na+].O>[NH2:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=2)[N:5]=[CH:4][C:3]=1[C:14](=[O:22])[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([C:25]2[CH:24]=[N:23][CH:28]=[CH:27][CH:26]=2)[CH:16]=1

참가 물질

7

반응물 4

HCID 62657Potassium Phosphate, TribasicHCID 27343783-Pyridinylboronic acidHCID 41980053-(1,3,2-Dioxaborinan-2-yl)pyridineHCID 114512375-Amino4-(3-bromobenzoyl)-1-(4-fluorophenyl)pyrazole

생성물 1

HCID 99506645-Amino-1-(4-fluorophenyl)-4-[3-(pyridin-3-yl)benzoyl]pyrazole

시약·촉매·용매 2

HCID 312751,4-Dioxane용매HCID 57417360Sodium chloride; water용매

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온도
85 °C

실험 절차

A mixture of 5-amino-4-(3-bromobenzoyl)-1-(4-fluorophenyl)pyrazole (0.9 g, 2.5 mmol) [prepared as described in Example 1 above], pyridine-3-boronic acid, 1,3-propanediol cyclic ester (0.5 g, 3 mmol), potassium phosphate (0.8 g, 3.73 mmol) and tetrakistriphosphine palladium (0.3 g, 0.25 mmol) in dioxane (20 ml) was heated at 85° C. under argon. After 16 h, the reaction mixture was cooled to room temperature and poured into brine. The product was extracted into ethyl acetate, dried over sodium sulfate and filtered. The organic layer was removed in vacuo and the residue was purified by flash chromatography (elution gradient: 40-80% ethyl acetate/hexane) to give 5-amino-1-(4-fluorophenyl)-4-[3-(pyridin-3-yl)benzoyl]-pyrazole (0.50 g) which was recrystallized from ethyl acetate (mpt. 222.2-223.0).

후처리

  1. temperaturethe reaction mixture was cooled to room temperature
  2. extractionThe product was extracted into ethyl acetate
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customThe organic layer was removed in vacuo
  6. customthe residue was purified by flash chromatography (elution gradient: 40-80% ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-d3c079038e7447bfa88d35db32334139
출처 데이터셋
uspto-grants-2001_11
특허 번호
US06316466B1

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