Dichloromethane → HCID 58495465, 화합물

HRID 1190989

반응식

HRID 1190989 반응식
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

참가 물질

6

반응물 4

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

생성물 1

HCID 58495465HCID 58495465, 화합물수율 76%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

반응 조건

온도
90 °C

실험 절차

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)+.

후처리

  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)

출처 및 근거

ORD 기록
ord-01ff898b45c445bcab9f091c7aabacf8
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08680091B2

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