Trifluoroacetic acid → 6-(2-Isopropyl-6-methoxy-1H-indol-3-ylmethyl)pyridine-2-carbonitrile

HRID 2409992ノート

反応式

HRID 2409992 の反応式
[C:1]([C:3]1[N:8]=[C:7]([CH2:9][CH:10]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][C:17]=2[NH:24]C(=O)OC(C)(C)C)[C:11](=O)[CH:12]([CH3:14])[CH3:13])[CH:6]=[CH:5][CH:4]=1)#[N:2].FC(F)(F)C(O)=O.C(=O)([O-])O.[Na+]>ClCCl>[CH:12]([C:11]1[NH:24][C:17]2[C:16]([C:10]=1[CH2:9][C:7]1[N:8]=[C:3]([C:1]#[N:2])[CH:4]=[CH:5][CH:6]=1)=[CH:21][CH:20]=[C:19]([O:22][CH3:23])[CH:18]=2)([CH3:14])[CH3:13]

参加物

5

反応物 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 86703307tert-Butyl {2-[1-(6-cyanopyridin-2-ylmethyl)-3-methyl-2-oxobutyl]-5-methoxyphenyl}carbamate

生成物 1

HCID 867033096-(2-Isopropyl-6-methoxy-1H-indol-3-ylmethyl)pyridine-2-carbonitrile収率 93.3%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of tert-butyl {2-[1-(6-cyanopyridin-2-ylmethyl)-3-methyl-2-oxobutyl]-5-methoxyphenyl}carbamate (269 mg) in dichloromethane (13 mL) was added trifluoroacetic acid (2.6 mL) under ice-cooling, and the mixture was stirred at room temperature for 2.75 hours. To the reaction mixture was added a saturated aqueous sodium hydrogen carbonate solution. The organic layer was separated, washed with saturated brine, dried over anhydrous magnesium 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 (181 mg). 1H-NMR (CDCl3) δ ppm: 1.28 (6H, d, J=7.0 Hz), 3.21-3.35 (1H, m), 3.83 (3H, s), 4.26 (2H, s), 6.73 (1H, dd, J=2.3, 8.8 Hz), 6.86 (1H, d, J=2.3 Hz), 7.19-7.29 (2H, m), 7.45-7.52 (1H, m), 7.55-7.64 (1H, m), 7.80 (1H, br s).

後処理

  1. temperaturecooling
  2. customThe organic layer was separated
  3. washwashed with saturated brine
  4. dry with materialdried over anhydrous magnesium 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-1642c346eddb44a3bba73950a2ec78d9
出典データセット
uspto-grants-2014_08
特許番号
US08815903B2

反応ノート

読み込み中…