1,1'-Carbonyldiimidazole → 6-bromo-1-(1H-indol-5-yl)-1H-imidazo[4,5-b]pyrazin-2(3H)-one

HRID 333157ノート

反応式

HRID 333157 の反応式
[Br:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[NH:14][CH:13]=[CH:12]3)[C:5]([NH2:18])=[N:4][CH:3]=1.[C:19](N1C=CN=C1)(N1C=CN=C1)=[O:20]>C1COCC1>[Br:1][C:2]1[N:7]=[C:6]2[N:8]([C:9]3[CH:10]=[C:11]4[C:15](=[CH:16][CH:17]=3)[NH:14][CH:13]=[CH:12]4)[C:19](=[O:20])[NH:18][C:5]2=[N:4][CH:3]=1

参加物

4

反応物 2

HCID 682631,1'-CarbonyldiimidazoleHCID 727136316-bromo-N2-(1H-indol-5-yl)pyrazine-2,3-diamine

生成物 1

HCID 727136326-bromo-1-(1H-indol-5-yl)-1H-imidazo[4,5-b]pyrazin-2(3H)-one収率 41%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
65 °C

実験手順

To a solution of 6-bromo-N2-(1H-indol-5-yl)pyrazine-2,3-diamine (0.450 g, 1.48 mmol) in THF (5 mL) was added carbonyldiimidazole (1.20 g, 7.40 mmol). The resulting mixture was heated at 65° C. for 48 hr, after which it was concentrated in vacuo and partitioned between EtOAc and H2O. The organic layer was separated, dried over MgSO4, filtered, and concentrated in vacuo to yield a residue that was purified via silica gel chromatography eluting with EtOAc to yield the title compound (0.20 g, 41%). HPLC retention time: 2.07 minutes; MS ESI (m/z): 330.2/332.2 (M+1)+, calc. 329.

後処理

  1. concentrationafter which it was concentrated in vacuo
  2. custompartitioned between EtOAc and H2O
  3. customThe organic layer was separated
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto yield a residue that
  8. customwas purified via silica gel chromatography
  9. washeluting with EtOAc

出典と根拠

ORDレコード
ord-5d5c31191c61420cb1a0f70cd3b14431
出典データセット
uspto-grants-2014_11
特許番号
US08877772B2

反応ノート

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