Methyl 4-hydroxy-3-methoxyphenylacetate → Methyl 2-(3-methoxy-4-(4-nitro-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazol-5-yloxy)phenyl)acetate

HRID 2423310ノート

反応式

HRID 2423310 の反応式
[CH3:1][O:2][C:3](=[O:14])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[C:7]([O:12][CH3:13])[CH:6]=1.[Na].Cl[C:17]1[C:18]([N+:34]([O-:36])=[O:35])=[C:19]2[C:23](=[CH:24][CH:25]=1)[N:22]([CH2:26][O:27][CH2:28][CH2:29][Si:30]([CH3:33])([CH3:32])[CH3:31])[N:21]=[CH:20]2>C1COCC1>[CH3:13][O:12][C:7]1[CH:6]=[C:5]([CH2:4][C:3]([O:2][CH3:1])=[O:14])[CH:10]=[CH:9][C:8]=1[O:11][C:17]1[C:18]([N+:34]([O-:36])=[O:35])=[C:19]2[C:23](=[CH:24][CH:25]=1)[N:22]([CH2:26][O:27][CH2:28][CH2:29][Si:30]([CH3:32])([CH3:33])[CH3:31])[N:21]=[CH:20]2

参加物

5

反応物 3

HCID 85214Methyl 4-hydroxy-3-methoxyphenylacetateHCID 5360545SodiumHCID 598648595-chloro-4-nitro-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazole

生成物 1

HCID 59864798Methyl 2-(3-methoxy-4-(4-nitro-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazol-5-yloxy)phenyl)acetate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒3 回

実験手順

To methyl-3-methoxy-4-hydroxyphenylacetate (0.062 g, 0.32 mmol) in dry THF (5 mL) under nitrogen was added sodium hexamethyldisylazide (1M solution in THF) (312 μl, 0.31 mmol). After 10 min. stirring at room temperature 5-chloro-4-nitro-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazole (93 mg, 0.28 mmol) in 5 mL of THF was added. The resulting mixture was stirred at reflux for 5 days. After that time the mixture was quenched with water and extracted with ethyl acetate (3×25 mL). The combined organic extracts were washed with brine, dried over magnesium sulfate and concentrated under reduced pressure. The desired product was isolated by chromatography (10% ethyl acetate/hexane). 1H NMR (400 MHz) (CDCl3) δ 8.40 (s, 1H); 7.70 (d, J=9.1 Hz, 1H); 7.05 (d, J=9.1 Hz, 1H); 6.95 (m, 2H), 6.84 (dd, J=1.5, 8.0 Hz, 1H); 5.75 (s, 2H); 3.82 (s, 3H), 3.62, s, 3H); 3.62 (s, 2H); 3.57 (t, J=8.0 Hz, 2H); 0.89 (t, J=8.0 Hz, 2H); 0.0 (s, 9H).

後処理

  1. additionwas added
  2. temperatureat reflux for 5 days
  3. customAfter that time the mixture was quenched with water
  4. extractionextracted with ethyl acetate (3×25 mL)
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-353d28c8e0194bc6a3ca81fd000ec45a
出典データセット
uspto-grants-2011_06
特許番号
US07960567B2

反応ノート

読み込み中…