Ethanol → 2-(2,5-Dimethylpyrrolyl)-6-(4-fluoro-naphth-1-yl)pyridine

HRID 842051노트

반응식

HRID 842051 반응식
[F:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5](B(O)O)=[CH:4][CH:3]=1.[CH3:15][C:16]1[NH:17][C:18]([CH3:28])=[CH:19][C:20]=1[C:21]1[CH:26]=[CH:25][CH:24]=[C:23](Br)[N:22]=1.C(=O)([O-])[O-].[Na+].[Na+].C(O)C>O>[CH3:15][C:16]1[NH:17][C:18]([CH3:28])=[CH:19][C:20]=1[C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([C:5]2[C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[C:2]([F:1])=[CH:3][CH:4]=2)[N:22]=1

참가 물질

6

반응물 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 27826754-Fluoro-1-naphthaleneboronic Acid (contains varying amounts of Anhydride)HCID 543198942-(2,5-Dimethylpyrrolyl)-6-bromopyridine

생성물 1

HCID 543666152-(2,5-Dimethylpyrrolyl)-6-(4-fluoro-naphth-1-yl)pyridine수율 700.4%

시약·촉매·용매 1

HCID 962Water용매2회

실험 절차

To a 50 mL round-bottomed flask equipped with condenser and N2 inlet were added 404 mg (2.13 mmol) 4-fluoronaphthalene-1-boronic acid, 534 mg (2.13 mmol) 2-(2,5-dimethylpyrrolyl)-6-bromopyridine, 902 mg (8.51 mmol) sodium carbonate, 150 mg tetrakistriphenylphosphine, 10 mL ethanol, and 2 mL water. The reaction was refluxed overnight, cooled, poured into water, and extracted into ethyl acetate. After combining with another run on a larger scale, the combined organic layer was washed with brine, dried over sodium sulfate, and evaporated. The residue was chromatographed on silica gel using hexane/ethyl acetate as eluant to afford 4.72 g (85%) of an oil. 1H-NMR (δ, CDCl3): 2.25 (s, 6H), 5.92 (s, 2H), 7.1-7.2 (m, 2H), 7.4-7.6 (m, 4H), 7.95 (t, J=8, 1H), 8.12 (d, J=8, 1H), 8.19 (d, J=8, 1H); 13C-NMR (δ, CDCl3): 13.41, 106.97, 108.82, 109.02, 120.18, 120.78, 120.84, 123.42, 123.81, 123.96, 125.48, 126.20, 127.32, 127.68, 127.76, 128.56, 132.35, 133.90, 138.22, 151.87, 157.82, 158.30, 160.34; MS (%): 317 (parent+1, 100); HRMS Calculated. for C21H18N2F (parent+1): 317.1454, Found: 317.1462.

후처리

  1. customTo a 50 mL round-bottomed flask equipped with condenser and N2 inlet
  2. temperatureThe reaction was refluxed overnight
  3. temperaturecooled
  4. extractionextracted into ethyl acetate
  5. washthe combined organic layer was washed with brine
  6. dry with materialdried over sodium sulfate
  7. customevaporated
  8. customThe residue was chromatographed on silica gel

출처 및 근거

ORD 기록
ord-5b3aa99df46243b9ba12d846c7f2c645
출처 데이터셋
uspto-grants-2002_04
특허 번호
US06372768B1

반응 노트

불러오는 중…