Triethylsilane → N,N-Dimethyl-4-((5-methyl-1H-imidazol-4-yl)methyl)naphthalen-1-amine

HRID 2381223ノート

反応式

HRID 2381223 の反応式
[CH3:1][N:2]([CH3:40])[C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([CH:13]([C:15]2[N:19](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[CH:18]=[N:17][C:16]=2[CH3:39])[OH:14])=[CH:5][CH:4]=1.C([SiH](CC)CC)C>C(O)(C(F)(F)F)=O>[CH3:40][N:2]([CH3:1])[C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([CH2:13][C:15]2[N:19]=[CH:18][NH:17][C:16]=2[CH3:39])=[CH:5][CH:4]=1.[CH3:1][N:2]([CH3:40])[C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([CH:13]([C:15]2[N:19]=[CH:18][NH:17][C:16]=2[CH3:39])[OH:14])=[CH:5][CH:4]=1

参加物

5

反応物 2

HCID 12052TriethylsilaneHCID 67026330(4-(dimethylamino)naphthalen-1-yl)(4-methyl-1-trityl-1H-imidazol-5-yl)methanol

生成物 2

HCID 25004152N,N-Dimethyl-4-((5-methyl-1H-imidazol-4-yl)methyl)naphthalen-1-amine収率 32%HCID 57965652(4-(dimethylamino)naphthalen-1-yl)(5-methyl-1H-imidazol-4-yl)methanol収率 25%

試薬・触媒・溶媒 1

HCID 6422Trifluoroacetic acid溶媒

実験手順

A solution of (4) (3.35 g, 6.40 mmol) in TFA (30 mL) was added triethylsilane (6 mL, 38.4 mmol). The reaction mixture was stirred at room temperature overnight. TFA was removed under vacuum. The residue was basified with 2 M sodium hydroxide to pH>7. The aqueous layer was extracted three times with chloroform/isopropanol (3:1200 mL). The pooled organic layers were dried over magnesium sulfate. The mixture was filtered and the solvents were removed under vacuum. The residue was purified by chromatography on silica gel with 2 to 5% saturated ammonia methanol in dichloromethane to give N,N-dimethyl-4-((5-methyl-1H-imidazol-4-yl)methyl)naphthalen-1-amine (5) (0.55 g, 2.07 mmol, 32% yield), and (4-(dimethylamino)naphthalen-1-yl)(5-methyl-1H-imidazol-4-yl)methanol (6) (0.45 g, 1.60 mmol, 25% yield).

後処理

  1. customTFA was removed under vacuum
  2. extractionThe aqueous layer was extracted three times with chloroform/isopropanol (3:1200 mL)
  3. dry with materialThe pooled organic layers were dried over magnesium sulfate
  4. filtrationThe mixture was filtered
  5. customthe solvents were removed under vacuum
  6. customThe residue was purified by chromatography on silica gel with 2 to 5% saturated ammonia methanol in dichloromethane

出典と根拠

ORDレコード
ord-5315613ac0324a558f2e79c9bf8dd180
出典データセット
uspto-grants-2012_09
特許番号
US08258167B2

反応ノート

読み込み中…