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

HRID 1869277노트

반응식

HRID 1869277 반응식
[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]

참가 물질

6

반응물 2

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

생성물 1

HCID 595960036-Chloro-5-iodo-3-nitropyridin-2-amine수율 69.5%

시약·촉매·용매 3

HCID 159865Silver sulfate촉매HCID 702Ethanol용매HCID 962Water용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-2cdc041e43b2453f9e01322939d6298f
출처 데이터셋
uspto-grants-2009_12
특허 번호
US07638530B2

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