Potassium Carbonate → 6-Methyl-3'-trifluoromethyl-[2,2']bipyridinyl-5-carbonitrile

HRID 2113630노트

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HRID 2113630 반응식
Cl[C:2]1[N:7]=[C:6]([C:8]2[C:13]([C:14]([F:17])([F:16])[F:15])=[CH:12][CH:11]=[CH:10][N:9]=2)[CH:5]=[CH:4][C:3]=1[C:18]#[N:19].[CH3:20]B(O)O.C([O-])([O-])=O.[K+].[K+].O1CCOCC1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[CH3:20][C:2]1[N:7]=[C:6]([C:8]2[C:13]([C:14]([F:17])([F:16])[F:15])=[CH:12][CH:11]=[CH:10][N:9]=2)[CH:5]=[CH:4][C:3]=1[C:18]#[N:19]

참가 물질

7

반응물 4

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 139377Methylboronic AcidHCID 586281896-Chloro-3'-trifluoromethyl-[2,2']bipyridinyl-5-carbonitrile

생성물 1

HCID 586281916-Methyl-3'-trifluoromethyl-[2,2']bipyridinyl-5-carbonitrile

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매

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온도
115 °C

실험 절차

In a sealed tube, dissolve 6-chloro-3′-trifluoromethyl-[2,2′]bipyridinyl-5-carbonitrile (242 mg, 0.853 mmol), CH3B(OH)2 (300 mg, 5.10 mmol), K2CO3 (1.6 g, 12 mmol), and Pd(PPh3)4 in a solution of dioxane (10 mL) and H2O (2 mL). Bubble argon through the mixture for 30 minutes and seal. Heat the mixture at 115° C. overnight. Cool the mixture to room temperature. Add H2O (20 mL) and extract with EtOAc (3×20 mL). Combine the organic extracts and wash with brine (60 mL). Dry the organic layer over Na2SO4 and remove the solvent under reduced pressure. Purify the crude product using silica gel chromatography eluting with EtOAc/hexane (1:1) to yield the title compound. MS 264.07 (M+1).

후처리

  1. customseal
  2. temperatureCool the mixture to room temperature
  3. extractionAdd H2O (20 mL) and extract with EtOAc (3×20 mL)
  4. washCombine the organic extracts and wash with brine (60 mL)
  5. dry with materialDry the organic layer over Na2SO4
  6. customremove the solvent under reduced pressure
  7. customPurify the crude product
  8. washeluting with EtOAc/hexane (1:1)

출처 및 근거

ORD 기록
ord-6fee241b24664faa8a6bba38cc01b94c
출처 데이터셋
uspto-grants-2008_10
특허 번호
US07432275B2

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