Sodium Carbonate → N-{4-[2-(4-fluorophenyl)pyrazolo[1,5-a]pyrimidin-3-yl]pyridin-2-yl}acetamide

HRID 570141ノート

反応式

HRID 570141 の反応式
Br[C:2]1[C:3]([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)=[N:4][N:5]2[CH:10]=[CH:9][CH:8]=[N:7][C:6]=12.CC1(C)C(C)(C)OB([C:26]2[CH:31]=[CH:30][N:29]=[C:28]([NH:32][C:33](=[O:35])[CH3:34])[CH:27]=2)O1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.C1CCC(P(C2CCCCC2)C2CCCCC2)CC1.C1CCC(P(C2CCCCC2)C2CCCCC2)CC1.[Cl-].[Cl-].[Pd+2]>[F:17][C:14]1[CH:15]=[CH:16][C:11]([C:3]2[C:2]([C:26]3[CH:31]=[CH:30][N:29]=[C:28]([NH:32][C:33](=[O:35])[CH3:34])[CH:27]=3)=[C:6]3[N:7]=[CH:8][CH:9]=[CH:10][N:5]3[N:4]=2)=[CH:12][CH:13]=1

参加物

6

反応物 3

HCID 10340Sodium CarbonateHCID 49760417N-(4-(tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)acetamideHCID 837474383-Bromo-2-(4-fluorophenyl)pyrazolo[1,5-a]pyrimidine

生成物 1

HCID 90387180N-{4-[2-(4-fluorophenyl)pyrazolo[1,5-a]pyrimidin-3-yl]pyridin-2-yl}acetamide収率 17%

試薬・触媒・溶媒 2

HCID 11556747Bis(tricyclohexylphosphine)palladium(II) Dichloride触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
150 °C

実験手順

3-Bromo-2-(4-fluorophenyl)pyrazolo[1,5-a]pyrimidine (150 mg, 0.51 mmol) and N-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl]acetamide (148 mg, 0.56 mmol, 1.1 eq) are dissolved in 1.5 mL 1,4-dioxan. To this mixture, bis(tricyclohexylphosphine)palladium(II)-dichloride (57 mg, 0.07 mmol, 0.15 eq) and 0.83 mL sodium carbonate solution (2 molar) are added. The reaction mixture is flushed with argon for 5 mins and then sealed. Next the mixture is heated for 30 min at 150° C. in the microwave (Biotage). The reaction mixture is then poured in water and extracted with dichloromethane (3×20 mL). The organic layer is dried over anhydrous magnesium sulphate, filtered and concentrated under reduced pressure. The crude material is purified by column chromatography using silica gel in heptane and ethyl acetate (1:0 to 1:1) as eluent and 0.03 g (17%) of N-{4-[2-(4-fluorophenyl)pyrazolo[1,5-a]pyrimidin-3-yl]pyridin-2-yl}acetamide are obtained as a white solid.

後処理

  1. customThe reaction mixture is flushed with argon for 5 mins
  2. customsealed
  3. additionThe reaction mixture is then poured in water
  4. extractionextracted with dichloromethane (3×20 mL)
  5. dry with materialThe organic layer is dried over anhydrous magnesium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe crude material is purified by column chromatography

出典と根拠

ORDレコード
ord-6fb2e7e00eaa4498aabd96ebb2001015
出典データセット
uspto-grants-2015_05
特許番号
US09023844B2

反応ノート

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