Iodine → 6-Chloro-5-iodo-3-nitropyridin-2-amine

HRID 1869277ノート

反応式

HRID 1869277 の反応式
[Cl:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][CH:3]=1.[I:12]I>CCO.O.[O-]S([O-])(=O)=O.[Ag+].[Ag+]>[Cl:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]=1[I:12]

参加物

6

反応物 2

HCID 807IodineHCID 27240356-Chloro-3-nitropyridin-2-ylamine

生成物 1

HCID 595960036-Chloro-5-iodo-3-nitropyridin-2-amine収率 69.5%

試薬・触媒・溶媒 3

HCID 159865Silver sulfate触媒HCID 702Ethanol溶媒HCID 962Water溶媒

実験手順

6-chloro-3-nitropyridin-2-amine (0.910 g, 5.24 mmol) was stirred in 15 ml EtOH. Iodine (1.33 g, 5.24 mmol) was added followed by addition of Ag2SO4 (1.64 g, 5.24 mmol). The reaction was stirred for 18 h and was then diluted with −30 ml of water and was filtered and washed with water. Air-drying afforded 1.09 g of 6-chloro-3-nitro-5-iodopyridin-2-amine. The iodide (1.09 g, 3.64 mmol), phenylboronic acid (0.444 g, 3.64 mmol), Pd(PPh3)4 (0.105 g, 0.091 mmol) and Na2CO3 (1.16 g, 10.9 mmol) were stirred in 4 ml of 3:1 dioxane/water and heated to reflux. After 4 h the reaction was diluted with water and extracted 3× with DCM. The combined organic extracts were dried over Na2SO4, filtered, and concentrated. The residue was triturated with ether, and the resulting solid was filtered and washed with ether. The resulting solid showed pure 6-chloro-3-nitro-5-phenylpyridin-2-amine (4-1). The filtrate was purified by flash column chromatography by dissolving in DCM and eluting with 95:5 DCM/EA. Afforded an additional 240 mg pure 6-chloro-3-nitro-5-phenylpyridin-2-amine (4-1). 1H NMR (CDCl3) δ 8.42 (s, 1H), 7.46-7.42 (m, 5H).

後処理

  1. filtrationwas filtered
  2. washwashed with water
  3. customAir-drying

出典と根拠

ORDレコード
ord-2cdc041e43b2453f9e01322939d6298f
出典データセット
uspto-grants-2009_12
特許番号
US07638530B2

反応ノート

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