Ethyl Acetate → 2-{7-[(4-Fluorophenyl)methoxy]-1,5-naphthyridin-3-yl}propan-2-ol

HRID 513960ノート

反応式

HRID 513960 の反応式
FC1C=CC(C[O:7][C:8]2[CH:17]=[C:16]3[C:11]([CH:12]=[C:13](C(OCC)=O)[CH:14]=[N:15]3)=[N:10][CH:9]=2)=CC=1.O[C:26]1C=C2C(C=C(C(OCC)=O)C=N2)=NC=1.C([O-])([O-])=O.[Cs+].[Cs+].[F:47][C:48]1[CH:55]=[CH:54][C:51]([CH2:52]Cl)=[CH:50][CH:49]=1.CCO[C:59]([CH3:61])=[O:60]>CN(C=O)C.O>[F:47][C:48]1[CH:55]=[CH:54][C:51]([CH2:52][O:7][C:8]2[CH:17]=[C:16]3[C:11]([CH:12]=[C:13]([C:59]([OH:60])([CH3:61])[CH3:26])[CH:14]=[N:15]3)=[N:10][CH:9]=2)=[CH:50][CH:49]=1

参加物

8

反応物 5

HCID 8857Ethyl AcetateHCID 96024-Fluorobenzyl chlorideHCID 10796Cesium carbonateHCID 90418013Ethyl 7-((4-fluorobenzyl)oxy)-1,5-naphthyridine-3-carboxylateHCID 136227102Ethyl 7-hydroxy-1,5-naphthyridine-3-carboxylate2 回

生成物 1

HCID 863016572-{7-[(4-Fluorophenyl)methoxy]-1,5-naphthyridin-3-yl}propan-2-ol収率 67%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

Ethyl 7-((4-fluorobenzyl)oxy)-1,5-naphthyridine-3-carboxylate. To a solution of ethyl 7-hydroxy-1,5-naphthyridine-3-carboxylate (Intermediate 4, 3.0 g, 13.75 mmol) in DMF (70 mL) was added Cs2CO3 (8.96 g, 0.03 mol), followed by 4-fluorobenzyl chloride (2.42 mL, 0.02 mol). The reaction was stirred at ambient temperature for 72 h. The crude reaction mixture was poured into EtOAc and water. The aqueous layer was extracted with EtOAc and the combined organic fractions were washed with brine and concentrated under reduced pressure onto silica. Purification (FCC, SiO2, 0-60%, EtOAc/hexanes) afforded the title compound as a white solid (3.0 g, 67%) 1H NMR (400 MHz, CDCl3) δ 9.45 (d, J=1.6 Hz, 1H), 8.97 (s, 1H), 8.85 (d, J=2.3 Hz, 1H), 7.72 (d, J=2.0 Hz, 1H), 7.48 (dd, J=5.5, 7.8 Hz, 2H), 7.12 (t, J=8.6 Hz, 2H), 5.22 (s, 2H), 4.48 (q, J=7.3 Hz, 2H), 1.46 (t, J=7.0 Hz, 3H). [M+H]=327.2

後処理

  1. customThe crude reaction mixture
  2. extractionThe aqueous layer was extracted with EtOAc
  3. washthe combined organic fractions were washed with brine
  4. concentrationconcentrated under reduced pressure onto silica
  5. customPurification (FCC, SiO2, 0-60%, EtOAc/hexanes)

出典と根拠

ORDレコード
ord-0f9b0438488c4c24827b9953cac86f6a
出典データセット
uspto-grants-2015_08
特許番号
US09102674B2

反応ノート

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