Sodium Bicarbonate → HCID 90391307, 화합물

HRID 1479833

반응식

HRID 1479833 반응식
Cl[C:2]1[CH:7]=[C:6]([C:8]#[N:9])[CH:5]=[C:4]([N:10]2[CH2:14][CH2:13][CH2:12][CH2:11]2)[N:3]=1.[F:15][C:16]([F:28])([F:27])[O:17][C:18]1[CH:23]=[CH:22][C:21](B(O)O)=[CH:20][CH:19]=1.C([O-])(O)=O.[Na+]>COCCOC.O>[N:10]1([C:4]2[CH:5]=[C:6]([C:8]#[N:9])[CH:7]=[C:2]([C:21]3[CH:20]=[CH:19][C:18]([O:17][C:16]([F:15])([F:27])[F:28])=[CH:23][CH:22]=3)[N:3]=2)[CH2:14][CH2:13][CH2:12][CH2:11]1

참가 물질

6

반응물 3

HCID 516892Sodium BicarbonateHCID 27343864-(Trifluoromethoxy)phenylboronic acidHCID 830745802-Chloro-6-(pyrrolidin-1-yl)pyridine-4-carbonitrile

생성물 1

HCID 90391307HCID 90391307, 화합물수율 77%

시약·촉매·용매 2

HCID 962Water용매HCID 80711,2-Dimethoxyethane용매

반응 조건

온도
100 °C

실험 절차

A solution of nitrile 25A (2.58 g, 12.5 mmol) in DME (90 mL) was added with 4-trifluoromethoxy phenyl boronic acid (2.64 g, 1.0 mol eq,) and NaHCO3 (3.15 g, 3 mol eq,) suspended in water (45 mL). The mixture was degassed under vacuum, then Palladium Tetrakis was added (catalytic amount) and the reaction was stirred at 100° C. under inert atmosphere for 12 h. The solvent was removed under reduced pressure and water was added to the residue (80 mL). The aqueous phase was extracted with EtOAc (3×60 mL) and the combined organic layer was washed with brine (80 mL) and dried over Na2SO4. The solvent was evaporated under vacuum to afford 26C as deliquescent yellow solid (3.2 g, 9.6 mmol, 77% Yield). 1HNMR (DMSO, 400 MHz) δ 1.85 (m, 4H), 3.42 (m, 4H), 6.38 (s, 1H), 7.08 (s, 1H), 7.38 (d, 2H, J=8), 8.05 (d, 2H, J=8).

후처리

  1. customThe mixture was degassed under vacuum
  2. additionPalladium Tetrakis was added (catalytic amount)
  3. customThe solvent was removed under reduced pressure and water
  4. additionwas added to the residue (80 mL)
  5. extractionThe aqueous phase was extracted with EtOAc (3×60 mL)
  6. washthe combined organic layer was washed with brine (80 mL)
  7. dry with materialdried over Na2SO4
  8. customThe solvent was evaporated under vacuum

출처 및 근거

ORD 기록
ord-084463b54b1a49479a6862e8155bae12
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09409864B2

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