Triethylamine → HCID 86707944、化合物

HRID 2400292ノート

反応式

HRID 2400292 の反応式
[CH3:1][CH:2]([C:5]1[N:6]([CH2:17][C:18]2[N:23]=[C:22]([C:24]([NH2:26])=O)[CH:21]=[CH:20][CH:19]=2)[C:7]2[C:12]([CH:13]=1)=[CH:11][C:10]([O:14][CH3:15])=[C:9]([Cl:16])[CH:8]=2)[CH2:3][CH3:4].C(N(CC)CC)C.FC(F)(F)C(OC(=O)C(F)(F)F)=O.C(=O)([O-])O.[Na+]>ClCCl>[CH3:1][CH:2]([C:5]1[N:6]([CH2:17][C:18]2[N:23]=[C:22]([C:24]#[N:26])[CH:21]=[CH:20][CH:19]=2)[C:7]2[C:12]([CH:13]=1)=[CH:11][C:10]([O:14][CH3:15])=[C:9]([Cl:16])[CH:8]=2)[CH2:3][CH3:4]

参加物

6

反応物 4

HCID 8471TriethylamineHCID 9845Trifluoroacetic anhydrideHCID 516892Sodium BicarbonateHCID 86707943HCID 86707943、化合物

生成物 1

HCID 86707944HCID 86707944、化合物収率 87.3%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of 6-[2-(butan-2-yl)-6-chloro-5-methoxyindol-1-ylmethyl]pyridine-2-carboxamide (118 mg) in dichloromethane (1.6 mL) were successively added triethylamine (0.225 mL) and trifluoroacetic anhydride (0.112 mL) under ice-cooling. This mixture was stirred at room temperature for 22 hours. To the reaction mixture was added saturated aqueous sodium hydrogen carbonate solution, followed by extraction with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane) to obtain the title compound (98 mg). 1H-NMR (CDCl3) δ ppm: 0.86 (3H, t, J=7.4 Hz), 1.24 (3H, d, J=6.8 Hz), 1.45-1.80 (2H, m), 2.60-2.75 (1H, m), 3.93 (3H, s), 5.40 (2H, s), 6.31 (1H, s), 6.50-6.65 (1H, m), 7.11 (1H, s), 7.14 (1H, s), 7.50-7.70 (2H, m).

後処理

  1. temperaturecooling
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane)

出典と根拠

ORDレコード
ord-6063af194ca54806aab880105097633d
出典データセット
uspto-grants-2014_08
特許番号
US08796247B2

反応ノート

読み込み中…