Ethyl bromopyruvate → Ethyl 6,8-dibromoimidazo[1,2-a]pyridine-2-carboxylate hydrobromide

HRID 2197548ノート

反応式

HRID 2197548 の反応式
[Br:1][C:2]1[C:3]([NH2:9])=[N:4][CH:5]=[C:6]([Br:8])[CH:7]=1.Br[CH2:11][C:12](=O)[C:13]([O:15][CH2:16][CH3:17])=[O:14]>C1COCC1>[BrH:1].[Br:8][C:6]1[CH:7]=[C:2]([Br:1])[C:3]2[N:4]([CH:11]=[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[N:9]=2)[CH:5]=1

参加物

4

反応物 2

HCID 66144Ethyl bromopyruvateHCID 988513,5-Dibromo-2-pyridylamine

生成物 1

HCID 67007442Ethyl 6,8-dibromoimidazo[1,2-a]pyridine-2-carboxylate hydrobromide収率 139.9%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A mixture of 3,5-dibromopyridin-2-amine (2.51 g, 10 mmol) and ethyl 3-bromo-2-oxopropanoate (2.5 g, 13 mmol) in THF (50 mL) was heated at reflux 48 hrs. The solution was evaporated and the residue triturated with ether and the resulting solid was filtered and dried to give ethyl 6,8-dibromoimidazo[1,2-a]pyridine-2-carboxylate hydrobromide (3.0 g, 69% yield). LCMS (Conditions C): 2.70 min (RT); (M+H)+=347.09 (60%), 349.09 (100%), 351. 08 (60%). 1H NMR, 400 MHz, CDCl3: δ 8.39 (d, 1.5 Hz, 1 H), 8.28 (s, 1 H), 7.67 (d, 1.5 Hz, 1 H), 4.46 (q, J=7.0 Hz, 2 H), 1.43 (t, J=7.0 Hz, 3 H).

後処理

  1. temperaturewas heated
  2. temperatureat reflux 48 hrs
  3. customThe solution was evaporated
  4. customthe residue triturated with ether
  5. filtrationthe resulting solid was filtered
  6. customdried

出典と根拠

ORDレコード
ord-e2fa2cff11e14de49761f444f6944ba5
出典データセット
uspto-grants-2012_12
特許番号
US08338604B2

反応ノート

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