Pyridine → 2-Cyclopentyl-6-methoxy-isonicotinonitrile

HRID 245082노트

반응식

HRID 245082 반응식
N1C=CC=CC=1.[CH:7]1([C:12]2[CH:13]=[C:14]([CH:18]=[C:19]([O:21][CH3:22])[N:20]=2)[C:15]([NH2:17])=O)[CH2:11][CH2:10][CH2:9][CH2:8]1.FC(F)(F)C(OC(=O)C(F)(F)F)=O>C(Cl)Cl>[CH:7]1([C:12]2[CH:13]=[C:14]([CH:18]=[C:19]([O:21][CH3:22])[N:20]=2)[C:15]#[N:17])[CH2:8][CH2:9][CH2:10][CH2:11]1

참가 물질

5

반응물 3

HCID 1049PyridineHCID 9845Trifluoroacetic anhydrideHCID 674914362-Cyclopentyl-6-methoxy-isonicotinamide

생성물 1

HCID 674912332-Cyclopentyl-6-methoxy-isonicotinonitrile수율 68%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

반응 조건

온도
0 °C

실험 절차

Pyridine (8.86 g, 91.3 mmol) is added to a solution of 2-cyclopentyl-6-methoxy-isonicotinamide (3.35 g, 15.2 mmol) in DCM (100 mL). The mixture is cooled to 0° C. before trifluoroacetic acid anhydride (9.58 g, 45.6 mmol) is added portionwise. The mixture is stirred at 0° C. for 1 h before it is diluted with DCM (100 mL) and washed with sat. aq. NaHCO3 solution (100 mL) and brine (100 mL). The separated org. phase is dried over MgSO4, filtered and concentrated. The crude product is purified by CC on silica gel eluting with heptane:EA 9:1 to give 2-cyclopentyl-6-methoxy-isonicotinonitrile (2.09 g) as pale yellow oil; LC-MS**: tR=0.80 min, [M+1]+=not detectable; 1H NMR (D6-DMSO): δ 1.61-1.82 (m, 6H), 1.94-2.03 (m, 2H), 3.16 (quint, J=7.8 Hz, 1H), 3.89 (s, 3H), 7.15 (s, 1H), 7.28 (s, 1H).

후처리

  1. additionis added portionwise
  2. washwashed with sat. aq. NaHCO3 solution (100 mL) and brine (100 mL)
  3. dry with materialphase is dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product is purified by CC on silica gel eluting with heptane:EA 9:1

출처 및 근거

ORD 기록
ord-91af2be7a5834b97adc972e37aac710a
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08658675B2

반응 노트

불러오는 중…