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

HRID 578867ノート

反応式

HRID 578867 の反応式
[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

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 1363371375,10,15,20-tetraphenyl-21H,23H-porphine iron (III) chloride触媒HCID 962Water溶媒HCID 1140Toluene溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-686eb7eeb4f8444a8859fffd3208465b
出典データセット
uspto-grants-2015_05
特許番号
US09040708B2

反応ノート

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