Dichloromethane → 8-Fluoro-6-methylphenanthridine

HRID 2224629노트

반응식

HRID 2224629 반응식
I[C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].FC(F)(F)S(O[C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][C:16]=1[C:22](=O)[CH3:23])(=O)=O.C(=O)([O-])[O-].[Na+].[Na+].ClCCl>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].CN(C)C=O>[F:21][C:18]1[CH:19]=[CH:20][C:15]2[C:16](=[C:22]([CH3:23])[N:4]=[C:3]3[C:2]=2[CH:8]=[CH:7][CH:6]=[CH:5]3)[CH:17]=1

참가 물질

7

반응물 4

HCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 119952-IodoanilineHCID 597176142-Acetyl-4-fluorophenyl trifluoromethanesulfonate

생성물 1

HCID 224823738-Fluoro-6-methylphenanthridine수율 27%

시약·촉매·용매 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 6228Dimethylformamide용매

반응 조건

온도
85 °C

실험 절차

1H NMR and TLC and no starting material was present (2-iodoaniline). 2-Acetyl-4-fluorophenyl trifluoromethanesulfonate (7.9 g, 28 mmol) was added to the reaction mixture, along with aqueous sodium carbonate (2 M, 61 mL, 122 mmol) and additional [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II), complex with dichloromethane (1:1) (1.0 g, 1.22 mmol) and N,N-dimethylformamide (50 mL). The reaction mixture was degassed several times and heated at 85° C. for 18 hours. The mixture was cooled to room temperature and poured into water (250 mL). The suspension was extracted with diethyl ether (2×250 mL). The combined organic extracts were dried over sodium sulfate, filtered, and concentrated in vacuo to give a brown oil. Purification by column chromatography (1:4 ethyl acetate:hexane) gave the product as a pale yellow solid (1.33 g, 27% ).

후처리

  1. customThe reaction mixture was degassed several times
  2. temperatureThe mixture was cooled to room temperature
  3. additionpoured into water (250 mL)
  4. extractionThe suspension was extracted with diethyl ether (2×250 mL)
  5. dry with materialThe combined organic extracts were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto give a brown oil
  9. customPurification by column chromatography (1:4 ethyl acetate:hexane)

출처 및 근거

ORD 기록
ord-32d051dcfba44ee28513e73f8714f83f
출처 데이터셋
uspto-grants-2008_05
특허 번호
US07378427B2

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