HCID 66935459、化合物 → HCID 66935781、化合物

HRID 1908794ノート

反応式

HRID 1908794 の反応式
[CH2:1]([O:3][C:4](=[O:17])[C:5]1[CH:10]=[C:9](Cl)[C:8]([N:12]([CH2:15][CH3:16])[CH2:13][CH3:14])=[N:7][CH:6]=1)[CH3:2].[CH2:18]([Zn]CC)[CH3:19]>O1CCOCC1.C1(C)C=CC=CC=1>[CH2:1]([O:3][C:4](=[O:17])[C:5]1[CH:10]=[C:9]([CH2:18][CH3:19])[C:8]([N:12]([CH2:15][CH3:16])[CH2:13][CH3:14])=[N:7][CH:6]=1)[CH3:2]

参加物

5

反応物 2

HCID 66935459HCID 66935459、化合物HCID 178418750HCID 178418750、化合物2 回

生成物 1

HCID 66935781HCID 66935781、化合物

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒2 回HCID 312751,4-Dioxane溶媒

実験手順

To a solution of 5-chloro-6-diethylamino-nicotinic acid ethyl ester (2.96 g, 11.5 mmol) in dioxane (50 mL), Pd(dppf) (470 mg, 0.576 mmol) is added under argon. To this mixture, diethyl zinc (8.53 g, 69.1 mmol, as a 1.1 M solution in toluene) is added dropwise. The mixture is stirred at 75° C. for 16 h before another portion of Pd(dppf) 94 mg, 0.115 mmol) and diethyl zinc (1.42 g, 11.5 mmol, as a 1.1 M solution in toluene) is added. Stirring is continued at 75° C. for 24 h. The reaction mixture is cooled to rt and carefully quenched with water. The mixture is filtered over celite and the filtrate is extracted twice with EA. The combined org. extracts are dried over MgSO4, filtered and concentrated. The crude product is purified by CC (heptane:EA 9:1) to give 6-diethylamino-5-ethyl-nicotinic acid ethyl ester (2.40 g) as a colourless oil; LC-MS: tR=0.78 min, [M+1]+=251.19; 1H NMR (CDCl3): δ 1.15 (t, J=7.0 Hz, 6H), 1.27 (t, J=7.3 Hz, 3H), 1.40 (t, J=7.3 Hz, 3H), 2.65 (q, J=7.5 Hz, 2H), 3.36 (q, J=7.0 Hz, 4H), 4.37 (q, J=7.0 Hz, 2H), 7.99 (d, J=2.3 Hz, 1H), 8.76 (d, J=2.3 Hz, 1H).

後処理

  1. customcarefully quenched with water
  2. filtrationThe mixture is filtered over celite
  3. extractionthe filtrate is extracted twice with EA
  4. dry with materialextracts are dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product is purified by CC (heptane:EA 9:1)

出典と根拠

ORDレコード
ord-c681151879a74196ac490b0ef22697b0
出典データセット
uspto-grants-2013_12
特許番号
US08598208B2

反応ノート

読み込み中…