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

HRID 1921337ノート

反応式

HRID 1921337 の反応式
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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 11979704Tetrakis(triphenylphosphine)palladium触媒HCID 887Methanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-fd0425637d6a4811b1ed1d9d2eb15a7e
出典データセット
uspto-grants-2012_05
特許番号
US08173682B2

反応ノート

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