Sodium Bicarbonate → (2-(2-Nitro-5-(piperidin-1-yl)phenyl)pyridin-4-yl)(3-(trifluoromethyl)phenyl)methanol

HRID 625262노트

반응식

HRID 625262 반응식
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)=[CH:6][C:5]=1[C:16]1[CH:17]=[C:18]([CH:21]=[CH:22][N:23]=1)[CH:19]=[O:20])([O-:3])=[O:2].[F:24][C:25]([F:35])([F:34])[C:26]1[CH:27]=[C:28]([Mg]Cl)[CH:29]=[CH:30][CH:31]=1.C([O-])(O)=O.[Na+]>C1COCC1>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)=[CH:6][C:5]=1[C:16]1[CH:17]=[C:18]([CH:19]([C:30]2[CH:29]=[CH:28][CH:27]=[C:26]([C:25]([F:35])([F:34])[F:24])[CH:31]=2)[OH:20])[CH:21]=[CH:22][N:23]=1)([O-:3])=[O:2]

참가 물질

5

반응물 3

HCID 516892Sodium BicarbonateHCID 867059382-(2-Nitro-5-(piperidin-1-yl)phenyl)isonicotinaldehydeHCID 178506175HCID 178506175, 화합물

생성물 1

HCID 86705939(2-(2-Nitro-5-(piperidin-1-yl)phenyl)pyridin-4-yl)(3-(trifluoromethyl)phenyl)methanol

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
0 °C

실험 절차

To a −78° solution of 110 mg of 2-(2-nitro-5-(piperidin-1-yl)phenyl)isonicotinaldehyde in 4 mL of THF was added 0.82 mL of a 1.0 M solution of 3-(trifluoromethyl)phenylmagnesium chloride in THF. After 5 min the solution was warmed to 0° C. and treated with 10 mL of a saturated aqueous solution of NaHCO3. The mixture was extracted with ethyl acetate and the organic extracts were washed with water and then with brine. The solution was dried (Na2SO4) and the solvent was evaporated. The residue was purified by silica gel chromatography eluting with 1:1 ethyl acetate/hexanes to give 123 mg of product. MS (ES, m/z) 458.2 [M+H]+.

후처리

  1. extractionThe mixture was extracted with ethyl acetate
  2. washthe organic extracts were washed with water
  3. dry with materialThe solution was dried (Na2SO4)
  4. customthe solvent was evaporated
  5. customThe residue was purified by silica gel chromatography
  6. washeluting with 1:1 ethyl acetate/hexanes

출처 및 근거

ORD 기록
ord-12d0d781420940fdb53c5b2a1dda8ab7
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09301951B2

반응 노트

불러오는 중…