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

HRID 507581노트

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HRID 507581 반응식
[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

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 178418476HCID 178418476, 화합물촉매HCID 887Methanol용매HCID 6344Dichloromethane용매

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온도
140 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-162f32b7cb2544d4b2a85e2fd1078312
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07786132B2

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