Dichloromethane → HCID 58495465、化合物

HRID 1190989

反応式

HRID 1190989 の反応式
Br[C:2]1[CH:3]=[CH:4][C:5]([C:8]#[N:9])=[N:6][CH:7]=1.[CH:10]1([CH:16]=[CH:17]B(O)O)[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1.C(Cl)Cl.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1>[CH:10]1(/[CH:16]=[CH:17]/[C:2]2[CH:3]=[CH:4][C:5]([C:8]#[N:9])=[N:6][CH:7]=2)[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1

参加物

6

反応物 4

HCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 8171545-Bromopyridine-2-carbonitrileHCID 41851492-Cyclohexylvinyl boronic acid

生成物 1

HCID 58495465HCID 58495465、化合物収率 76%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

反応条件

温度
90 °C

実験手順

Combine a mixture of 5-bromo-2-cyano-pyridine (2 g, 10.93 mmol), 2-cyclohexylvinyl boronic acid (2.52 g, 16.39 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) complex with DCM (446 mg, 0.546 mmol) and 2M aqueous Na2CO3 (18.2 mL, 36.07 mmol) in 1,4-dioxane (110 mL). Purge with nitrogen and heat at 90° C. overnight. Cool the reaction to room temperature and partition between EtOAc and water. Separate the aqueous phase and extract with EtOAc. Dry the combined organic extracts over MgSO4, filter and concentrate in vacuo. Purify by chromatography on silica gel (120 g, pre-packed cartridge) eluting stepwise with hexane/EtOAc (1:0 over 5 min, 49:1 over 5 min and 19:1 over 5 min; 50 mL/min) to obtain the desired intermediate (1.76 g, 76%). MS (APCI+) m/z: 213 (M+H)+.

後処理

  1. customPurge with nitrogen
  2. temperatureCool
  3. customthe reaction to room temperature
  4. custompartition between EtOAc and water
  5. customSeparate the aqueous phase
  6. extractionextract with EtOAc
  7. dry with materialDry the combined organic extracts over MgSO4
  8. filtrationfilter
  9. concentrationconcentrate in vacuo
  10. customPurify by chromatography on silica gel (120 g, pre-packed cartridge)
  11. washeluting stepwise with hexane/EtOAc (1:0 over 5 min, 49:1 over 5 min and 19:1 over 5 min; 50 mL/min)

出典と根拠

ORDレコード
ord-01ff898b45c445bcab9f091c7aabacf8
出典データセット
uspto-grants-2014_03
特許番号
US08680091B2

関連ノート

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