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

HRID 432005노트

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HRID 432005 반응식
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

참가 물질

6

반응물 2

HCID 6077842-(Tributylstannyl)pyridine2회HCID 219426553-(5-Bromofuran-2-yl)-benzonitrile2회

생성물 1

HCID 219424103-(5-(2-Pyridyl)-2-furyl)-benzonitrile수율 76%

시약·촉매·용매 3

HCID 6097231Methanidylbenzene;palladium(2+);triphenylphosphane;chloride촉매HCID 178418397HCID 178418397, 화합물촉매HCID 1140Toluene용매2회

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온도
110 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-f4ff63ca18914d17a7609457c8247337
출처 데이터셋
uspto-grants-2003_12
특허 번호
US06660753B2

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