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

HRID 2113630ノート

反応式

HRID 2113630 の反応式
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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒

反応条件

温度
115 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-6fee241b24664faa8a6bba38cc01b94c
出典データセット
uspto-grants-2008_10
特許番号
US07432275B2

反応ノート

読み込み中…