Cesium carbonate → Diethyl 4-(2,4,6-trimethoxyphenyl)pyridine-2,6-dicarboxylate

HRID 1097175노트

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HRID 1097175 반응식
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[C:5]([O:11][CH3:12])[C:4]=1B(O)O.Br[C:17]1[CH:22]=[C:21]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[N:20]=[C:19]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH:18]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>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>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[C:5]([O:11][CH3:12])[C:4]=1[C:17]1[CH:18]=[C:19]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[N:20]=[C:21]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH:22]=1

참가 물질

6

반응물 3

HCID 10796Cesium carbonateHCID 41979962,4,6-Trimethoxyphenylboronic acidHCID 13794409Diethyl 4-bromopyridine-2,6-dicarboxylate

생성물 1

HCID 66814130Diethyl 4-(2,4,6-trimethoxyphenyl)pyridine-2,6-dicarboxylate

시약·촉매·용매 2

HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 6228Dimethylformamide용매

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온도
95 °C

실험 절차

2,4,6-trimethoxyphenylboronic acid (2.12 g, 10.0 mmol) and diethyl 4-bromopyridine-2,6-dicarboxylate (3.33 g, 11.0 mmol) were dissolved in dry DMF (50 mL). Caesium carbonate (4.56 g, 14.0 mmol) and tetrakis(triphenylphosphine)-palladium(0) (0.23 g, 0.20 mmol) were added, and the mixture was deaerated with argon. The mixture was heated at 95° C. for 48 h. The mixture was allowed to cool to room temperature and filtered. The filtrate was concentrated in vacuo, the residue was dissolved in chloroform (60 mL) and washed with 10% aq. citric acid and water, dried over Na2SO4 and concentrated. Purification was performed on silica gel (eluent petroleum ether bp 40-60° C.; ethyl acetate 5:3→2:5, v/v). Yield was 2.09 g (54%). 1H NMR (CDCl3): δ 1.45 (6H, t, J 7.1); 3.74 (6H, s); 3.90 (3H, s); 4.49 (4H, q, J 7.1); 6.22 (2H, s); 8.28 (2H, s). IR (film)/cm−1 1743, 1610 (C═O); 1339, 1238, 1128 (C—O). ESI-MS: [M+H]+ 390.19 calc. for C20H24NO7+ 390.15.

후처리

  1. temperatureto cool to room temperature
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated in vacuo
  4. dissolutionthe residue was dissolved in chloroform (60 mL)
  5. washwashed with 10% aq. citric acid and water
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. customPurification

출처 및 근거

ORD 기록
ord-a71d2297210b40d9bf7bb0013ffbb2b2
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08143057B2

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