Potassium Phosphate, Tribasic → methyl 5-(4-fluorophenyl)-4-ethyl-2-formyl-1H-pyrrole-3-carboxylate

HRID 1785005ノート

反応式

HRID 1785005 の反応式
[CH2:1]([C:3]1[C:4]([C:11]([O:13][CH3:14])=[O:12])=[C:5]([CH:9]=[O:10])[NH:6][C:7]=1I)[CH3:2].[O-]P([O-])([O-])=O.[K+].[K+].[K+].[F:23][C:24]1[CH:29]=[CH:28][C:27](B(O)O)=[CH:26][CH:25]=1>C(COC)OC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:23][C:24]1[CH:29]=[CH:28][C:27]([C:7]2[NH:6][C:5]([CH:9]=[O:10])=[C:4]([C:11]([O:13][CH3:14])=[O:12])[C:3]=2[CH2:1][CH3:2])=[CH:26][CH:25]=1

参加物

6

反応物 3

HCID 62657Potassium Phosphate, TribasicHCID 2856454-Fluorophenylboronic acidHCID 11278208Methyl 4-ethyl-2-formyl-5-iodo-1H-pyrrole-3-carboxylate

生成物 1

HCID 11346399methyl 5-(4-fluorophenyl)-4-ethyl-2-formyl-1H-pyrrole-3-carboxylate

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
85 °C

実験手順

Methyl 4-ethyl-2-formyl-5-iodo-1H-pyrrole-3-carboxylate was obtained following the procedures described in Example 3. To a solution of methyl 4-ethyl-2-formyl-5-iodo-1H-pyrrole-3-carboxylate (0.123 g, 0.40 mmol) in dimethoxyethane (4.0 mL) was added K3PO4 (0.426 g, 2.00 mmol), Pd(PPh3)4 (0.0463 g, 0.04 mmol), and 4-fluorophenylboronic acid (0.0842 g, 0.60 mmol). The reaction was deoxygenated by bubbling argon through the solution prior to being heated to 85° C. and refluxed for 16 h under argon. After cooling to ambient temperature, the reaction was filtrated through a pad of silica gel and concentration. The resultant residue was dissolved in acetonitrile and purified by reverse phase HPLC. Proton NMR for the product was consistent with the title compound. 1H NMR (500 MHz, CDCl3) δ 10.15 (s, 1H); 7.43 (dd, J=3.4, 5.2 Hz, 2H); 7.18 (app t, 8.6 Hz, 2H); 3.94 (s, 3H); 2.80 (q, J=7.4 Hz, 2H); 1.22 (t, J=7.4 Hz, 3H). HRMS (ES) exact mass calculated C15H15FNO3 (M+H): 276.1312. Found 276.1264

後処理

  1. customThe reaction was deoxygenated
  2. customby bubbling argon through the solution
  3. temperaturerefluxed for 16 h under argon
  4. temperatureAfter cooling to ambient temperature
  5. filtrationthe reaction was filtrated through a pad of silica gel and concentration
  6. dissolutionThe resultant residue was dissolved in acetonitrile
  7. custompurified by reverse phase HPLC

出典と根拠

ORDレコード
ord-d66db81322d54060919d458613af4f4e
出典データセット
uspto-grants-2009_03
特許番号
US07504429B2

反応ノート

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