2-(Tributylstannyl)pyridine → 3-(5-(2-Pyridyl)-2-furyl)-benzonitrile

HRID 432005ノート

反応式

HRID 432005 の反応式
Br[C:2]1[O:6][C:5]([C:7]2[CH:8]=[C:9]([CH:12]=[CH:13][CH:14]=2)[C:10]#[N:11])=[CH:4][CH:3]=1.C([Sn](CCCC)(CCCC)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=1)CCC>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[CH2-]C1C=CC=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cl-].[Pd+2]>[N:21]1[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=1[C:2]1[O:6][C:5]([C:7]2[CH:8]=[C:9]([CH:12]=[CH:13][CH:14]=2)[C:10]#[N:11])=[CH:4][CH:3]=1

参加物

6

反応物 2

HCID 6077842-(Tributylstannyl)pyridine2 回HCID 219426553-(5-Bromofuran-2-yl)-benzonitrile2 回

生成物 1

HCID 219424103-(5-(2-Pyridyl)-2-furyl)-benzonitrile収率 76%

試薬・触媒・溶媒 3

HCID 6097231Methanidylbenzene;palladium(2+);triphenylphosphane;chloride触媒HCID 178418397HCID 178418397、化合物触媒HCID 1140Toluene溶媒2 回

反応条件

温度
110 °C

実験手順

Similarly, Pd(PPh3)4 (22 mg, 0.019 mmol) was added to a solution of 3-(5-bromofuran-2-yl)-benzonitrile (35 mg, 0.14 mmol) and 2-tributylstannylpyridine (71 mg, 0.19 mmol) in toluene (2 mL) under argon. In a similar manner, benzylbis(triphenylphosphine)palladium(II) chloride (10.5 mg, 0.014 mmol) was added to a solution of 3-(5-bromofuran-2-yl)-benzonitrile (35 mg, 0.14 mmol) and 2-tributylstannylpyridine (75 mg, 0.20 mmol) in toluene (2 mL) under argon. Both solutions were stirred at 110° C. for 18 h. After cooling to room temperature, the mixtures were combined since TLC of both reactions proved to be identical. The solvent was removed in vacuo from the combined product. Chromatography (5g silica gel SPE tube, dichloromethane) followed by triturating with 10% ethyl acetate in hexanes afforded 26.2 mg (38%) of 3-(5-(2-pyridyl)-2-furyl)-benzonitrile. 1H-NMR (CDCl3), δ (ppm): 8.63 (d, 1H), 8.05 (s, 1H), 7.96 (d, 1H), 7.77 (m, 3H), 7.54 (m, 2H), 7.20 (m, 1H), 6.89 (d, 1H).

後処理

  1. temperatureAfter cooling to room temperature
  2. customThe solvent was removed in vacuo from the combined product
  3. customby triturating with 10% ethyl acetate in hexanes

出典と根拠

ORDレコード
ord-f4ff63ca18914d17a7609457c8247337
出典データセット
uspto-grants-2003_12
特許番号
US06660753B2

反応ノート

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