Sodium Bicarbonate → HCID 90391307、化合物

HRID 1479833ノート

反応式

HRID 1479833 の反応式
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

参加物

6

反応物 3

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

生成物 1

HCID 90391307HCID 90391307、化合物収率 77%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
100 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-084463b54b1a49479a6862e8155bae12
出典データセット
uspto-grants-2016_08
特許番号
US09409864B2

反応ノート

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