Triethylamine → 4-[(1E)-3-Cyclohexylprop-1-en-1-yl]-2-fluoroaniline

HRID 576068노트

반응식

HRID 576068 반응식
Br[C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([F:9])[CH:3]=1.[CH2:10]([CH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1)[CH:11]=[CH2:12].CC1C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(N(CC)CC)C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(OCC)(=O)C.C1(C)C=CC=CC=1>[CH:13]1([CH2:10]/[CH:11]=[CH:12]/[C:2]2[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([F:9])[CH:3]=2)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1

참가 물질

8

반응물 4

HCID 8471TriethylamineHCID 75027AllylcyclohexaneHCID 80271Tri-o-tolylphosphineHCID 1230504-Bromo-2-fluoroaniline

생성물 1

HCID 867072764-[(1E)-3-Cyclohexylprop-1-en-1-yl]-2-fluoroaniline수율 69%

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

실험 절차

Toluene (5 mL) was added to 4-bromo-2-fluoroaniline (950 mg, 5.00 mmol), allylcyclohexane (1.15 mL, 7.50 mmol), palladium acetate (112 mg, 0.50 mmol), tris(2-methylphenyl)phosphine (457 mg, 1.50 mmol) and triethylamine (2.09 mL, 15.0 mmol), and the mixture was stirred, followed by heating to reflux for 10 hr. After cooling, ethyl acetate was added thereto, the mixture was filtered through Celite (registered trademark), and then the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane only→hexane:ethyl acetate=9:1) to afford the title compound as a pale yellow oil (805 mg).

후처리

  1. temperatureby heating
  2. temperatureto reflux for 10 hr
  3. temperatureAfter cooling
  4. filtrationthe mixture was filtered through Celite (registered trademark)
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography (hexane only→hexane

출처 및 근거

ORD 기록
ord-3b399ca8f6234bd1a544d2fcf1048114
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09035059B2

반응 노트

불러오는 중…