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

HRID 2409992노트

반응식

HRID 2409992 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-1642c346eddb44a3bba73950a2ec78d9
출처 데이터셋
uspto-grants-2014_08
특허 번호
US08815903B2

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