Toluene → 3-(5-Ethyl-6-methoxy-2,4-dimethylpyridin-3-yl)benzonitrile

HRID 1921337노트

반응식

HRID 1921337 반응식
Br[C:2]1[C:3]([CH3:13])=[C:4]([CH2:11][CH3:12])[C:5]([O:9][CH3:10])=[N:6][C:7]=1[CH3:8].[C:14]([C:16]1[CH:17]=[C:18](B(O)O)[CH:19]=[CH:20][CH:21]=1)#[N:15].C(=O)([O-])[O-].[Na+].[Na+].C1(C)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.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd].CO>[CH2:11]([C:4]1[C:3]([CH3:13])=[C:2]([C:20]2[CH:21]=[C:16]([CH:17]=[CH:18][CH:19]=2)[C:14]#[N:15])[C:7]([CH3:8])=[N:6][C:5]=1[O:9][CH3:10])[CH3:12]

참가 물질

7

반응물 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 27343253-Cyanophenylboronic acidHCID 674921695-Bromo-3-ethyl-2-methoxy-4,6-dimethylpyridine

생성물 1

HCID 674922613-(5-Ethyl-6-methoxy-2,4-dimethylpyridin-3-yl)benzonitrile수율 14%

시약·촉매·용매 2

HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 887Methanol용매

실험 절차

A mixture of 5-bromo-3-ethyl-2-methoxy-4,6-dimethylpyridine (254 mg, 1.75 mmol), 3-cyanophenylboronic acid (254 mg, 1.75 mmol), palladium tetrakis(triphenylphosphine) (81.2 mg, 0.07 mmol), 2M aq sodium carbonate (1.15 mL), toluene (10 mL) and methanol (0.7 mL) is reacted following the procedures of Step 4, Example 5. The crude product is purified by HPLC in two runs eluting with a gradient of acetonitrile-20 to 5% water ramping @ 0.5% per min. Product containing fractions from both runs are combined and concentrated to afford 3-(5-ethyl-6-methoxy-2,4-dimethylpyridin-3-yl)benzonitrile (44 mg, 14%) as an oil. LC/MS: MS m/e=267 (M+H); RT 4.41 min.

후처리

  1. customis reacted
  2. customThe crude product is purified by HPLC in two runs
  3. washeluting with a gradient of acetonitrile-20 to 5% water ramping @ 0.5% per min
  4. additionProduct containing fractions from both runs
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-fd0425637d6a4811b1ed1d9d2eb15a7e
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08173682B2

반응 노트

불러오는 중…