4-Vinylpyridine → 3-(1-Boc-2-(s)-pyrrolidinyl-methoxy)-5-(4-pyridinyl-ethenyl)pyridine

HRID 365875ノート

反応式

HRID 365875 の反応式
[C:1]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:13][O:14][C:15]1[CH:16]=[N:17][CH:18]=[C:19](Br)[CH:20]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH:22]([C:24]1[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=1)=[CH2:23].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C([O-])(O)=O.[Na+]>C(#N)C.CCN(CC)CC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:1]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:13][O:14][C:15]1[CH:16]=[N:17][CH:18]=[C:19]([CH:23]=[CH:22][C:24]2[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=2)[CH:20]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

参加物

8

反応物 4

HCID 75024-VinylpyridineHCID 80271Tri-o-tolylphosphineHCID 516892Sodium BicarbonateHCID 15480235(S)-2-((5-Bromopyridin-3-yloxy)methyl)pyrrolidine-1-carboxylic acid tert-butyl ester

生成物 1

HCID 540343103-(1-Boc-2-(s)-pyrrolidinyl-methoxy)-5-(4-pyridinyl-ethenyl)pyridine収率 80%

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 6342Acetonitrile溶媒HCID 8471Triethylamine溶媒

反応条件

温度
100 °C

実験手順

To a solution of 3-(1-BOC-2-(S)-pyrrolidinylmethoxy)-5-bromopyridine (300 mg, 0.84 mmol) in acetonitrile (10 mL) and NEt3 (1 mL) was added 4-vinylpyridine(0.15 mL, 1.34 mmol), palladium acetate (28 mg, 0.13 mmol) and tri-o-tolylphosphine (141 mg). The reaction mixture was heated in a sealed tube at 100° C. for 16 h. After cooling to room temperature, saturated NaHCO3 solution was added. The mixture was extracted with EtOAc (2X). The combined organic solvent was dried (MgSO4), concentrated and chromatographed (silica gel; hexane/EtOAc, 2:1 to 1:2) to afford an oil (255 mg, 80%): 1H NMR (CDCl3, 300 Hz) δ1.50 (s, 9H), 1.90 (m, 1H), 2.00-2.10 (m, 2H), 3.30-3.50 (m, 2H), 4.00 (m, 1H), 4.14-4.24 (m, 2H), 4.28 (m, 1H), 7.10 (m, 1H), 7.24 (m, 1H), 7.36-7.40 (m, 3H), 8.26 (s, 1H), 8.30 (s, 1H), 8.60 (d, 2H, J=6.5 Hz); MS (CI/NH3) m/z 382 (M+H)+.

後処理

  1. temperatureAfter cooling to room temperature
  2. extractionThe mixture was extracted with EtOAc (2X)
  3. dry with materialThe combined organic solvent was dried (MgSO4)
  4. concentrationconcentrated
  5. customchromatographed (silica gel; hexane/EtOAc, 2:1 to 1:2)

出典と根拠

ORDレコード
ord-84eb9f36a7014b589ea3914f8539a35d
出典データセット
uspto-grants-2000_10
特許番号
US06127386

反応ノート

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