Tetrahydrofuran → HCID 58551097、化合物

HRID 1908097ノート

反応式

HRID 1908097 の反応式
[O:1]=[C:2]1[CH:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[CH:5]=[CH:4][NH:3]1.C([O-])([O-])=O.[K+].[K+].C1[CH2:22][O:21][CH2:20][CH2:19]1.Br[CH2:24][CH2:25][O:26][CH3:27]>CN(C=O)C>[CH3:22][O:21][CH2:20][CH2:19][N:3]1[CH:4]=[CH:5][C:6]([C:8]([O:10][CH3:11])=[O:9])=[CH:7][C:2]1=[O:1].[CH3:27][O:26][CH2:25][CH2:24][O:1][C:2]1[CH:7]=[C:6]([CH:5]=[CH:4][N:3]=1)[C:8]([O:10][CH3:11])=[O:9]

参加物

7

反応物 4

HCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 809722-Bromoethyl methyl etherHCID 280755Methyl 2-oxo-1,2-dihydropyridine-4-carboxylate

生成物 2

HCID 58551097HCID 58551097、化合物収率 44%HCID 58551310Methyl 2-(2-methoxyethoxy)pyridine-4-carboxylate

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

Methyl 2-oxo-1H-pyridine-4-carboxylate (2.00 g, 13.1 mmol), K2CO3 (3.61 g, 26.1 mmol), THF (48 mL), DMF (38 mL) and 1-bromo-2-methoxy-ethane (3.63 g, 2.45 mL, 26.1 mmol) were combined and the mixture was stirred at 80° C. for 2 d. The reaction was filtered using ethyl acetate and the solvent was evaporated under reduced pressure and the residue was purified by column chromatography on silica gel (0-100% ethyl acetate in hexane) to yield methyl 1-(2-methoxyethyl)-2-oxo-1,2-dihydropyridine-4-carboxylate [(1.22 g, 44%), ESI-MS m/z calc. 211.1. found 212.3 (M+1)+; Retention time: 0.57 minutes (3 min run); 1H NMR (400 MHz, DMSO) δ 8.35 (d, J=5.2 Hz, 1H), 7.41 (d, J=5.2 Hz, 1H), 7.21 (s, 1H), 4.47-4.36 (m, 2H), 3.89 (s, 3H), 3.71-3.64 (m, 2H), 3.30 (s, 3H)] and methyl 2-(2-methoxyethoxy)isonicotinate [(405 mg), ESI-MS m/z calc. 211.1. found 212.1 (M+1)+; Retention time: 1.04 minutes (3 min run); 1H NMR (400 MHz, DMSO) δ 7.75 (d, J=7.0 Hz, 1H), 6.86 (s, 1H), 6.55 (d, J=7.0 Hz, 1H), 4.09 (t, J=5.2 Hz, 2H), 3.85 (s, 3H), 3.58 (t, J=5.2 Hz, 2H), 3.23 (s, 3H)].

後処理

  1. filtrationThe reaction was filtered
  2. customthe solvent was evaporated under reduced pressure
  3. customthe residue was purified by column chromatography on silica gel (0-100% ethyl acetate in hexane)

出典と根拠

ORDレコード
ord-4ef1af3d858544ca8ae76a6dc85f0618
出典データセット
uspto-grants-2013_12
特許番号
US08598164B2

反応ノート

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