2-Amino-5-cyanopyridine → 2-(5-Bromofuran-2-yl)-imidazo[1,2-a]pyridine-6-carbonitrile

HRID 2113554ノート

反応式

HRID 2113554 の反応式
[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][N:3]=1.Br[CH2:11][C:12]([C:14]1[O:15][C:16]([Br:19])=[CH:17][CH:18]=1)=O>C(O)C>[Br:19][C:16]1[O:15][C:14]([C:12]2[N:1]=[C:2]3[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][N:3]3[CH:11]=2)=[CH:18][CH:17]=1

参加物

4

反応物 2

HCID 8182602-Amino-5-cyanopyridineHCID 125376692-Bromo-1-(5-bromofuran-2-yl)ethan-1-one

生成物 1

HCID 692538532-(5-Bromofuran-2-yl)-imidazo[1,2-a]pyridine-6-carbonitrile収率 74%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A mixture of 6-Amino-nicotinonitrile (1.19 g, 10 mmol) and 2-Bromo-1-(5-bromofuran-2-yl)-ethanone (2.66 g, 10 mmol) in ethanol (50 mL) was refluxed for 24 h. The precipitate was filtered and neutralized with aqueous NaHCO3 solution. The precipitate was filtered and dried to furnish 3a in 74% yield, mp 212-214° C. (EtOH). 1H NMR (DMSO-d6); δ 6.75 (d, J=3.6 Hz, 1H), 6.98 (d, J=3.6 Hz, 1H), 7.54 (d, J=8.4 Hz, 1H), 7.71 (d, J=8.4 Hz, 1H), 8.29 (s, 1H), 9.30 (s, 1H). 13C NMR; δ 150.5, 144.2, 137.3, 134.3, 125.4, 121.9, 117.2, 116.9, 113.9, 110.4, 109.8, 97.2. MS (m/z, rel.int.); 288 (M+, 100), 161 (8). Anal. Calcd. for 3a (C12H6BrN3O): C % 50.03, H % 2.10. Found: C % 49.97, H % 2.17.

後処理

  1. temperaturewas refluxed for 24 h
  2. filtrationThe precipitate was filtered
  3. filtrationThe precipitate was filtered
  4. customdried

出典と根拠

ORDレコード
ord-cca7e578d3e5470bacc2afa162f0338b
出典データセット
uspto-grants-2008_10
特許番号
US07432278B2

反応ノート

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