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

HRID 853809노트

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HRID 853809 반응식
[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]

참가 물질

7

반응물 4

HCID 962WaterHCID 517044Potassium AcetateHCID 27374944-Bromo-3-methylbenzonitrileHCID 111164736-(2-Furyl)nicotinonitrile

생성물 1

HCID 694598846-[5-(4-Cyano-2-methyl-phenyl)-furan-2-yl]-nicotinonitrile수율 40%

시약·촉매·용매 2

HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 6228Dimethylformamide용매

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온도
120 °C

실험 절차

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.

후처리

  1. customThe precipitate that formed
  2. customwas collected
  3. dissolutiondissolved in methylene chloride
  4. customto remove Pd
  5. customThe solution was evaporated
  6. filtrationthe solid was filtered
  7. custompurified

출처 및 근거

ORD 기록
ord-b7447061b6e34fca99b6a0845c334269
출처 데이터셋
uspto-grants-2007_08
특허 번호
US07256203B2

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