Sodium hydride → 2-(6-bromo-9-chloro-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-phenanthro[9,10-d]imidazol-2-yl)isophthalonitrile

HRID 549491ノート

反応式

HRID 549491 の反応式
[Br:1][C:2]1[CH:3]=[C:4]2[C:26](=[CH:27][CH:28]=1)[C:12]1[NH:13][C:14]([C:16]3[C:23]([C:24]#[N:25])=[CH:22][CH:21]=[CH:20][C:17]=3[C:18]#[N:19])=[N:15][C:11]=1[C:10]1[CH:9]=[CH:8][C:7]([Cl:29])=[CH:6][C:5]2=1.[H-].[Na+].[CH3:32][Si:33]([CH3:40])([CH3:39])[CH2:34][CH2:35][O:36][CH2:37]Cl>C1COCC1>[Br:1][C:2]1[CH:28]=[CH:27][C:26]2[C:12]3[N:13]=[C:14]([C:16]4[C:23]([C:24]#[N:25])=[CH:22][CH:21]=[CH:20][C:17]=4[C:18]#[N:19])[N:15]([CH2:37][O:36][CH2:35][CH2:34][Si:33]([CH3:40])([CH3:39])[CH3:32])[C:11]=3[C:10]3[C:5](=[CH:6][C:7]([Cl:29])=[CH:8][CH:9]=3)[C:4]=2[CH:3]=1

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 178509773HCID 178509773、化合物

生成物 1

HCID 866148732-(6-bromo-9-chloro-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-phenanthro[9,10-d]imidazol-2-yl)isophthalonitrile収率 94.6%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 2-(6-bromo-9-chloro-1H-phenanthro[9,10-d]imidazol-2-yl)isophthalonitrile (5 g, 10.9 mmol) from Example 36 in THF (30 mL) was added NaH (60% dispersion in oil, 1.31 g, 32.7 mmol). The mixture was stirred at room temperature for 10 minutes, after which 2-(trimethylsilyl)ethoxymethylchloride (5.8 mL, 32.7 mmol) was added. After 1 hour, the reaction was quenched by slow addition of water. The aqueous layer was extracted with ethyl acetate, the organic layer washed once with water, once with brine, dried over anhydrous MgSO4 and concentrated to afford crude 2-(6-bromo-9-chloro-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-phenanthro[9,10-d]imidazol-2-yl)isophthalonitrile (6.06 g).

後処理

  1. waitAfter 1 hour
  2. customthe reaction was quenched by slow addition of water
  3. extractionThe aqueous layer was extracted with ethyl acetate
  4. washthe organic layer washed once with water, once with brine
  5. dry with materialdried over anhydrous MgSO4
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-ba3988a0aa864a228081b821174ebda4
出典データセット
uspto-grants-2011_05
特許番号
US07943649B2

反応ノート

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