Sodium Iodide → Methyl 4-amino-5-fluoro-6-(4-iodophenyl)-3-vinylpicolinate

HRID 516578ノート

反応式

HRID 516578 の反応式
[B-](F)(F)(F)F.N#[O+].[NH2:8][C:9]1[C:14]([F:15])=[C:13]([C:16]2[CH:21]=[CH:20][C:19](N)=[CH:18][CH:17]=2)[N:12]=[C:11]([C:23]([O:25][CH3:26])=[O:24])[C:10]=1[CH:27]=[CH2:28].[I-:29].[Na+].S([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl.O.CC#N>[NH2:8][C:9]1[C:14]([F:15])=[C:13]([C:16]2[CH:21]=[CH:20][C:19]([I:29])=[CH:18][CH:17]=2)[N:12]=[C:11]([C:23]([O:25][CH3:26])=[O:24])[C:10]=1[CH:27]=[CH2:28]

参加物

8

反応物 4

HCID 5238Sodium IodideHCID 24437Sodium SulfiteHCID 11137142Nitrilooxonium tetrafluoroborateHCID 90409711Methyl 4-amino-6-(4-aminophenyl)-5-fluoro-3-vinylpicolinate

生成物 1

HCID 90408914Methyl 4-amino-5-fluoro-6-(4-iodophenyl)-3-vinylpicolinate収率 23.09%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6342Acetonitrile溶媒HCID 6344Dichloromethane溶媒2 回

反応条件

温度
0 °C

実験手順

To a 0° C. suspension of nitrosyl tetrafluoroborate (0.041 g, 0.348 mmol) in CH2Cl2 (1 mL) was added a solution of methyl 4-amino-6-(4-aminophenyl)-5-fluoro-3-vinylpicolinate (0.1 g, 0.348 mmol) in a 1:1 mixture of CH2Cl2 and CH3CN (4 mL). The reaction mixture was stirred at 0° C. for 30 min, then a solution of sodium iodide (0.261 g, 1.740 mmol) dissolved in a minimum of water was added and the reaction was stirred at 20° C. for 30 min. The mixture was then poured into a 10% aqueous solution of sodium sulfite and extracted with EtOAc (3×). The combined organic layers were dried over Na2SO4, filtered and concentrated. The residue was purified by flash column chromatography (SiO2, hexanes/EtOAc gradient) followed by preparative reverse phase HPLC (water/acetonitrile gradient) to afford the title compound as a white solid (32 mg, 0.080 mmol, 23.09%).

後処理

  1. additionwas added
  2. stirringthe reaction was stirred at 20° C. for 30 min
  3. extractionextracted with EtOAc (3×)
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by flash column chromatography (SiO2, hexanes/EtOAc gradient)

出典と根拠

ORDレコード
ord-26343ad24d7149b1a11f8013d2f730df
出典データセット
uspto-grants-2015_08
特許番号
US09113629B2

反応ノート

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