Sodium Bicarbonate → HCID 86679808, 화합물

HRID 1754563노트

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HRID 1754563 반응식
CC(C)([O-])C.[K+].[Cl:7][C:8]1[C:9]([F:16])=[CH:10][C:11]([I:15])=[C:12]([CH:14]=1)[NH2:13].[O:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH:18]1[N:23]1[CH:27]=[C:26]([C:28](F)=[O:29])[CH:25]=[N:24]1.C([O-])(O)=O.[Na+]>C1COCC1>[Cl:7][C:8]1[C:9]([F:16])=[CH:10][C:11]([I:15])=[C:12]([NH:13][C:28]([C:26]2[CH:25]=[N:24][N:23]([CH:18]3[CH2:19][CH2:20][CH2:21][CH2:22][O:17]3)[CH:27]=2)=[O:29])[CH:14]=1

참가 물질

6

반응물 4

HCID 516892Sodium BicarbonateHCID 23665647Potassium tert-butoxideHCID 247872515-Chloro-4-fluoro-2-iodobenzenamineHCID 86039217HCID 86039217, 화합물

생성물 1

HCID 86679808HCID 86679808, 화합물수율 31%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

Potassium t-butoxide (12.52 g, 111.6 mmol) is added at room temperature to a solution of 5-chloro-4-fluoro-2-iodoaniline (5.0 g, 22.3 mmol) in 250 mL of anhydrous THF under nitrogen. After stirring for 15 minutes, a solution of 1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazole-4-carboxylic acid fluoride (5.67 g, 24.6 mmol) in 30 mL of anhydrous THF is added dropwise. The reaction mixture is stirred for 4 hours at room temperature and then poured into saturated aqueous NaHCO3 solution and extracted with EtOAc. The organic phase is washed with saturated aqueous NaCl solution, dried over Na2SO4 and concentrated to dryness. After purification by flash chromatography on silica (cyclohexene/EtOAc: 95/5 to 80/20), a red solid is obtained, which is purified by flash chromatography on amine phase (DCM) to give 2.84 g of a white solid (yield: 31%).

후처리

  1. stirringThe reaction mixture is stirred for 4 hours at room temperature
  2. extractionextracted with EtOAc
  3. washThe organic phase is washed with saturated aqueous NaCl solution
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated to dryness
  6. customAfter purification by flash chromatography on silica (cyclohexene/EtOAc: 95/5 to 80/20)
  7. customa red solid is obtained
  8. customwhich is purified by flash chromatography on amine phase (DCM)

출처 및 근거

ORD 기록
ord-82f952c4b9d14ea888cf2bc662e58f7a
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09169246B2

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