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

HRID 2216895Notes

Reaction equation

HRID 2216895 reaction equation
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

Participants

6

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 609723122784-59-4CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent2×

Conditions

Temperature
110 °C

Procedure

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 (5 g 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).

Workup

  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

Sources & evidence

ORD record
ord-b44cbda1e1984e52b340e94f689de0b5
Source dataset
uspto-grants-2006_09
Patent number
US07112595B2

Reaction notes

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