Chloroacetaldehyde → 6-Iodoimidazo(1,2-a)pyridine

HRID 751296ノート

反応式

HRID 751296 の反応式
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([I:8])=[CH:4][N:3]=1.Cl[CH2:10][CH:11]=O>C(#N)C>[I:8][C:5]1[CH:6]=[CH:7][C:2]2[N:3]([CH:10]=[CH:11][N:1]=2)[CH:4]=1

参加物

4

反応物 2

HCID 33ChloroacetaldehydeHCID 885792-Pyridinamine, 5-iodo-

生成物 1

HCID 27643276-Iodoimidazo(1,2-a)pyridine収率 66.1%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

Reflux a solution of 2-amino-5-iodo-pyridine (Tetrahedron 2002, 58, 2885-2890; 1.5 g, 6.82 mmol) and 50% aqueous chloroacetaldehyde (1.56 mL, 12.3 mmol) in acetonitrile (150 mL) for 14 h. Cool, concentrate, and dissolve the residue in 1:1 saturated aqueous sodium bicarbonate/dichloromethane. Extract the aqueous layer with dichloromethane, combine the organic layers, and concentrate. Flash chromatography using appropriate ethyl acetate/methanol mixtures gives 1.1 g (66%) of the subtitled compound as a light green solid. TOF MS ES+ exact mass calculated for C7H51N2 (p+1): m/z=244.9576; Found: 244.9564. 1H NMR (400 MHz, DMSO-d6) δ 8.9 (s, 1H), 7.86 (s, 1H), 7.52 (s, 1H), 7.40 (d, J=9 Hz, 1H), 7.36 (d, J=9.2, H).

後処理

  1. temperatureCool
  2. concentrationconcentrate
  3. dissolutiondissolve the residue in 1:1 saturated aqueous sodium bicarbonate/dichloromethane
  4. extractionExtract the aqueous layer with dichloromethane
  5. concentrationconcentrate

出典と根拠

ORDレコード
ord-b3bcf2a8b2fd44acbbb5d3ae5515a8e3
出典データセット
uspto-grants-2008_07
特許番号
US07405299B2

反応ノート

読み込み中…