Sodium Carbonate → 4-[2-(2-Hydroxyethyl)-1-benzofuran-4-yl]benzonitrile

HRID 1064739노트

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HRID 1064739 반응식
[C:1]([C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1)#[N:2].[C:12]1([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)C=CC=[CH:14][C:13]=1P(C1CCCCC1)C1CCCCC1.[C:37]([O-:40])([O-])=O.[Na+].[Na+].C1C=CC=CC=1.C([OH:51])C>C(Cl)Cl.C([O-])(=O)C.C([O-])(=O)C.[Pd+2]>[OH:51][CH2:14][CH2:13][C:12]1[O:40][C:37]2[CH:36]=[CH:35][CH:34]=[C:33]([C:6]3[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][CH:5]=3)[C:32]=2[CH:31]=1

참가 물질

7

반응물 4

HCID 10340Sodium CarbonateHCID 27342162-(Dicyclohexylphosphino)biphenylHCID 27343264-Cyanophenylboronic acidHCID 21965192Npc112006

생성물 1

HCID 222746244-[2-(2-Hydroxyethyl)-1-benzofuran-4-yl]benzonitrile수율 55%

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 6344Dichloromethane용매

반응 조건

온도
75 °C

실험 절차

The product from Example 85C (0.1 g, 0.32 mmol) in 8 mL of benzene/ethanol (2:1), was treated with 4-cyanophenylboronic acid (0.052 g, 0.35 mmol), palladium diacetate (0.0032 mmol), bipheny-2yl-dicyclohexylphosphine (0.0048 mmol) and Na2CO3 (2M, 0.87 mmol) and heated at 75° C. for 14 hours. The mixture was diluted with 100 mL of CH2Cl2 and washed successively with water (100 mL) and brine (100 mL), dried over sodium sulfate, filtered, and the filtrate was evaporated under reduced pressure. The residue was purified by chromatography over silica using CH2Cl2 to provide the title compound (55% yield). 1HNMR (300 MHz, CDCl3) δ 3.10 (m, 2H), 4.05 (m, 2H), 6.62 (s, 1H), 6.90 (m, 1H), 7.25 (m, 2H), 7.52 (m, 2H), 7.73(m, 2H). MS (CDI) m/z 264 (M+H)+.

후처리

  1. washwashed successively with water (100 mL) and brine (100 mL)
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. customthe filtrate was evaporated under reduced pressure
  5. customThe residue was purified by chromatography over silica

출처 및 근거

ORD 기록
ord-d63c9cdc96874b61bbe5160adbc43656
출처 데이터셋
uspto-grants-2005_11
특허 번호
US06969730B2

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