Sodium Carbonate → 5-(2-Chloropyrimidin-4-yl)thiophene-2-carbonitrile

HRID 2267357ノート

反応式

HRID 2267357 の反応式
[C:1]([C:3]1[S:7][C:6](B(O)O)=[CH:5][CH:4]=1)#[N:2].[Cl:11][C:12]1[N:17]=[C:16](Cl)[CH:15]=[CH:14][N:13]=1.C([O-])([O-])=O.[Na+].[Na+].O1CCOCC1>C(Cl)Cl.CO.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:11][C:12]1[N:17]=[C:16]([C:6]2[S:7][C:3]([C:1]#[N:2])=[CH:4][CH:5]=2)[CH:15]=[CH:14][N:13]=1

参加物

8

反応物 4

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 775312,4-DichloropyrimidineHCID 41987435-Cyanothiophene-2-boronic acid

生成物 1

HCID 574288365-(2-Chloropyrimidin-4-yl)thiophene-2-carbonitrile

試薬・触媒・溶媒 3

HCID 178418476HCID 178418476、化合物触媒HCID 887Methanol溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
140 °C

実験手順

A solution of 0.22 g (1.4 mmol) of 5-cyanothiophen-2-ylboronic acid, 0.21 g (1.4 mmol) of 2,4-dichloropyrimidine and 49 mg (0.070 mmol) of bis(triphenylphosphine)palladium(II) chloride in 2 mL of a 2 M Na2CO3 aqueous solution and 5 mL of 1,4-dioxane was as heated in a microwave for 30 min at 140° C., then cooled to rt, diluted with CH2Cl2 and MeOH, and dried over MgSO4. The organic solvent was removed in vacuo, and the resulting solid was purified by flash chromatography eluting with a linear gradient of 50% EtOAc in hexane to neat EtOAc to deliver the title compound. MS (M+H)+ 222.

後処理

  1. temperaturecooled to rt
  2. dry with materialdried over MgSO4
  3. customThe organic solvent was removed in vacuo
  4. customthe resulting solid was purified by flash chromatography
  5. washeluting with a linear gradient of 50% EtOAc in hexane to neat EtOAc

出典と根拠

ORDレコード
ord-8936163b2f184a618c1cf9619478f6ac
出典データセット
uspto-grants-2010_12
特許番号
US07858785B2

反応ノート

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