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

HRID 588375ノート

反応式

HRID 588375 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 312751,4-Dioxane溶媒

反応条件

温度
85 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-151e3f75b2c54638be3ddc4985ba5cf2
出典データセット
uspto-grants-2016_01
特許番号
US09227956B2

反応ノート

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