Dichloromethane → Ethyl 4-(pyrazolo[1,5-a]pyrimidin-3-yl)benzoate

HRID 588375노트

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HRID 588375 반응식
[CH2:1]([O:3][C:4]([C:6]1[CH:11]=[CH:10][C:9](B(O)O)=[CH:8][CH:7]=1)=[O:5])[CH3:2].Br[C:16]1[CH:17]=[N:18][N:19]2[CH:24]=[CH:23][CH:22]=[N:21][C:20]=12.C(Cl)Cl.C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.O>[N:18]1[N:19]2[CH:24]=[CH:23][CH:22]=[N:21][C:20]2=[C:16]([C:9]2[CH:10]=[CH:11][C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])=[CH:7][CH:8]=2)[CH:17]=1

참가 물질

7

반응물 4

HCID 6344DichloromethaneHCID 10796Cesium carbonateHCID 27343504-Ethoxycarbonylphenylboronic acidHCID 122032083-Bromopyrazolo(1,5-a)pyrimidine

생성물 1

HCID 117652969Ethyl 4-(pyrazolo[1,5-a]pyrimidin-3-yl)benzoate

시약·촉매·용매 2

HCID 962Water용매2회HCID 312751,4-Dioxane용매

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온도
85 °C

실험 절차

Water (160 mL) was added dropwise at room temperature to a mixture of 4-ethoxycarbonylphenylboronic acid (50 g, 0.26 mol), 3-bromopyrazolo[1,5-a]pyrimidine (56.25 g, 0.28 mol), Pd(ddpf)Cl2.CH2Cl2 (4.25 g, 5.21 mmol), and Cs2CO3 (169.42 g, 0.52 mol) in 1,4-dioxane (1 L). The reaction mixture was then heated 85° C. for 4 h. The reaction mixture was cooled, poured into water and extracted with EtOAc (2×300 mL). The combined organic layers were dried over Na2SO4, filtered, and the filtrate was concentrated under reduced pressure. The crude product was purified by silica gel chromatography eluting with a gradient of petroleum ether: EtOAc (100:10 to 3:1) to deliver the title compound (64 g, 93%) as a yellow solid.

후처리

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted with EtOAc (2×300 mL)
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe crude product was purified by silica gel chromatography
  7. washeluting with a gradient of petroleum ether: EtOAc (100:10 to 3:1)

출처 및 근거

ORD 기록
ord-151e3f75b2c54638be3ddc4985ba5cf2
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09227956B2

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