Potassium Iodide → 4-(Biphenyl-4-ylaminomethyl)-5-methyl-furan-2-carboxylic acid methyl ester

HRID 460102노트

반응식

HRID 460102 반응식
[I-].[K+].[C:3]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:8]=[CH:7][C:6]([NH2:9])=[CH:5][CH:4]=1.[CH3:16][O:17][C:18]([C:20]1[O:21][C:22]([CH3:27])=[C:23]([CH2:25]Cl)[CH:24]=1)=[O:19].C(=O)([O-])[O-].[K+].[K+]>O1CCCC1>[CH3:16][O:17][C:18]([C:20]1[O:21][C:22]([CH3:27])=[C:23]([CH2:25][NH:9][C:6]2[CH:5]=[CH:4][C:3]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)=[CH:8][CH:7]=2)[CH:24]=1)=[O:19]

참가 물질

6

반응물 4

HCID 4875Potassium IodideHCID 71024-AminobiphenylHCID 11430Potassium CarbonateHCID 914782Methyl 4-(chloromethyl)-5-methylfuran-2-carboxylate

생성물 1

HCID 588241954-(Biphenyl-4-ylaminomethyl)-5-methyl-furan-2-carboxylic acid methyl ester수율 71.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

Potassium iodide (32 mg) and a solution of biphenyl-4-ylamine (74 mg, 0.438 mmoles) in tetrahydrofuran (1 ml) was added to a mixture of 4-chloromethyl-5-methyl-furan-2-carboxylic acid methyl ester (159)(75 mg, 0.398 mmoles) and potassium carbonate (83 mg) in tetrahydrofuran (1 ml). The mixture was stirred at room temperature under an argon atmosphere for 16 hours, and then refluxed with the exclusion of light for 16 hours. After cooling, the mixture was concentrated and the residue was purified by by flash chromatography, using a gradient elution of petrol/diethyl ether 9:1 v/v to 4:1 v/v, to afford compound 158(91 mg). LC/MS System A; Rt=3.93 mins, m/z (ES+)=322(M+H for C20H19NO3).

후처리

  1. temperaturerefluxed with the exclusion of light for 16 hours
  2. temperatureAfter cooling
  3. concentrationthe mixture was concentrated
  4. customthe residue was purified by by flash chromatography
  5. washa gradient elution of petrol/diethyl ether 9:1 v/v to 4:1 v/v

출처 및 근거

ORD 기록
ord-60e6b15a06644dc7ad77916cb1b2572a
출처 데이터셋
uspto-grants-2007_03
특허 번호
US07196089B2

반응 노트

불러오는 중…