Ethanamine, 2,2,2-trifluoro- → 1-[3-Chloro-5-[2-(trifluoromethyl)cyclopropyl]-2-pyridyl]cyclopropanecarbonitrile

HRID 578867노트

반응식

HRID 578867 반응식
[Cl:1][C:2]1[C:3]([C:10]2([C:13]#[N:14])[CH2:12][CH2:11]2)=[N:4][CH:5]=[C:6]([CH:8]=[CH2:9])[CH:7]=1.[F:15][C:16]([F:20])([F:19])[CH2:17]N.N([O-])=O.[Na+].[Cl-].[NH4+]>C1(C)C=CC=CC=1.[Fe](Cl)(Cl)Cl.C1(C2C3NC(C(C4C=CC=CC=4)=C4N=C(C(C5C=CC=CC=5)=C5NC(=C(C6C=CC=CC=6)C6C=CC=2N=6)C=C5)C=C4)=CC=3)C=CC=CC=1.O>[Cl:1][C:2]1[C:3]([C:10]2([C:13]#[N:14])[CH2:11][CH2:12]2)=[N:4][CH:5]=[C:6]([CH:8]2[CH2:9][CH:17]2[C:16]([F:20])([F:19])[F:15])[CH:7]=1

참가 물질

8

반응물 4

HCID 9773Ethanamine, 2,2,2-trifluoro-HCID 25517Ammonium ChlorideHCID 23668193Sodium NitriteHCID 895443761-(3-Chloro-5-vinyl-2-pyridyl)cyclopropanecarbonitrile

생성물 1

HCID 895441591-[3-Chloro-5-[2-(trifluoromethyl)cyclopropyl]-2-pyridyl]cyclopropanecarbonitrile수율 61.2%

시약·촉매·용매 3

HCID 1363371375,10,15,20-tetraphenyl-21H,23H-porphine iron (III) chloride촉매HCID 962Water용매HCID 1140Toluene용매

실험 절차

1.4 g 1-(3-chloro-5-vinyl-2-pyridyl)cyclopropanecarbonitrile (step 1) was dissolved in 2.0 ml toluene and 14 mg 5,10,15,20-tetraphenyl-21H,23H-porphine iron(III) chloride was added. Then 30 ml water was added, followed by 1.4 g 2,2,2-trifluoroethanamine and 1.1 g sodium nitrite. The reaction mixture was stirred for 3 hours at ambient temperature. Then saturated ammonium chloride solution was added and the mixture was extracted with dichloromethane. The organic phase was washed with water, dried over anhydrous sodium sulfate, filtered and concentrated. Crude material was obtained as a dark oil, which was purified by flash chromatography on silica gel with heptane/ethyl acetate as a solvent. Thus, 1.2 g of 1-[3-chloro-5-[2-(trifluoromethyl)cyclopropyl]-2-pyridyl]cyclopropanecarbonitrile was obtained as a brown oil. 1H-NMR (CDCl3): 8.25 ppm (s, 1H), 7.44 ppm (s, 1H), 2.35 ppm (m, 1H), 1.85 ppm (m, 1H), 1.75 ppm (m, 2H), 1.60 ppm (m, 2H), 1.50 ppm (m, 1H), 1.24 ppm (m, 2H).

후처리

  1. extractionthe mixture was extracted with dichloromethane
  2. washThe organic phase was washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customCrude material was obtained as a dark oil, which
  7. customwas purified by flash chromatography on silica gel with heptane/ethyl acetate as a solvent

출처 및 근거

ORD 기록
ord-686eb7eeb4f8444a8859fffd3208465b
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09040708B2

반응 노트

불러오는 중…