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

HRID 490404ノート

反応式

HRID 490404 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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 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).

後処理

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

出典と根拠

ORDレコード
ord-c5029745b2414d7ca6194c167cca5751
出典データセット
uspto-grants-2009_05
特許番号
US07528157B2

反応ノート

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