Water → 6-[5-(4-Cyano-2-methyl-phenyl)-furan-2-yl]-nicotinonitrile

HRID 853809Notes

Reaction equation

[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:13]=[CH:12][C:9]([C:10]#[N:11])=[CH:8][N:7]=1.Br[C:15]1[CH:22]=[CH:21][C:18]([C:19]#[N:20])=[CH:17][C:16]=1[CH3:23].C([O-])(=O)C.[K+].O>CN(C=O)C.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:19]([C:18]1[CH:21]=[CH:22][C:15]([C:5]2[O:1][C:2]([C:6]3[CH:13]=[CH:12][C:9]([C:10]#[N:11])=[CH:8][N:7]=3)=[CH:3][CH:4]=2)=[C:16]([CH3:23])[CH:17]=1)#[N:20]

Participants

Conditions

Temperature: 120 °C

Procedure

Referring now to Scheme 6, a mixture of 1 (680 mg, 4 mmol), 4-bromo-3-methylbenzonitrile (784 mg, 4 mmol), tetrakis(triphenylphosphine)-palladium(0) (228 mg) and potassium acetate (981.5 mg, 10 mmol) in dry DMF (15 mL) was heated under nitrogen at 120° C. for 16 h. The reaction mixture then poured onto cold-water. The precipitate that formed was collected, dissolved in methylene chloride, and the solution was passed through celite to remove Pd. The solution was evaporated, the solid was filtered and purified to afford 28 (SiO2, hexanes/EtOAc, 1:1), yield 40%, mp 233–234° C. 1H nmr (DMSO-d6); δ 2.61 (s, 3H), 7.25 (d, J=3.6 Hz, 1H), 7.51 (d, J=3.6 Hz, 1H), 7.77 (d, J=8.1 Hz, 1H), 7.82 (s, 1H). 8.03–8.07 (m, 2H), 8.36 (dd, J=8.1, 2.1 Hz, 1H), 9.02 (d, J=2.1 Hz, 1H). 13C nmr; δ 153.2, 152.7, 151.9, 150.2, 140.8, 135.6, 134.8, 132.5, 129.8, 127.3, 118.3, 117.0, 114.4, 110.2, 106.8, 21.2.

Workup

customThe precipitate that formed
customwas collected
dissolutiondissolved in methylene chloride
customto remove Pd
customThe solution was evaporated
filtrationthe solid was filtered
custompurified

Sources & evidence

ORD record: ord-b7447061b6e34fca99b6a0845c334269
Source dataset: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07256203B2

Reaction notes

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