Toluene → 3-(6-Methoxy-2-methylpyridin-3-yl)benzonitrile

HRID 1921324노트

반응식

HRID 1921324 반응식
[C:1]([C:3]1[CH:4]=[C:5](B(O)O)[CH:6]=[CH:7][CH:8]=1)#[N:2].Br[C:13]1[C:14]([CH3:21])=[N:15][C:16]([O:19][CH3:20])=[CH:17][CH:18]=1.C1(C)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>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.[Pd].CO>[CH3:20][O:19][C:16]1[N:15]=[C:14]([CH3:21])[C:13]([C:5]2[CH:4]=[C:3]([CH:8]=[CH:7][CH:6]=2)[C:1]#[N:2])=[CH:18][CH:17]=1

참가 물질

7

반응물 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 27343253-Cyanophenylboronic acidHCID 107981463-Bromo-6-methoxy-2-methylpyridine

생성물 1

HCID 674923163-(6-Methoxy-2-methylpyridin-3-yl)benzonitrile수율 61%

시약·촉매·용매 2

HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 887Methanol용매

실험 절차

To a nitrogen flushed mixture of 3-cyanophenylboronic acid (5.0 g, 34 mmol), 3-bromo-6-methoxy-2-methylpyridine (4.6 g, 22.7 mmol) and palladium tetrakis(triphenylphosphine) (789 mg, 0.68 mmol) is added toluene (150 mL), methanol (12 mL) and sodium carbonate (22.7 mmol) and the mixture is heated overnight at reflux. The cooled reaction is concentrated and the residue is purified by chromatography eluting with cyclohexane-3.2 to 9% ethyl acetate. Product containing fractions are combined and concentrated to afford 3-(6-methoxy-2-methylpyridin-3-yl)benzonitrile (3.09 g, 61% yield) as a white solid. LC/MS: MS m/e=225 (M+H); RT 3.58 min; 1H NMR (CDCl3, δ ppm) 7.65 (1H, m), 7.60 (1H, m), 7.56 (2H, m), 7.40 (1H, d), 6.63 (1H, d), 3.98 (3H, s), 2.40 (3H, s).

후처리

  1. customTo a nitrogen flushed
  2. temperaturethe mixture is heated overnight
  3. temperatureat reflux
  4. customThe cooled reaction
  5. concentrationis concentrated
  6. customthe residue is purified by chromatography
  7. washeluting with cyclohexane-3.2 to 9% ethyl acetate
  8. additionProduct containing fractions
  9. concentrationconcentrated

출처 및 근거

ORD 기록
ord-53f2c18e32ef496485cad58d7c578025
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08173682B2

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