Bromine → HCID 11459593、化合物

HRID 891854ノート

反応式

HRID 891854 の反応式
[F:1][C:2]([C:5]1[CH:10]=[N:9][N:8]2[CH:11]=[CH:12][N:13]=[C:7]2[N:6]=1)([CH3:4])[CH3:3].C([O-])(=O)C.[Na+].[Br:19]Br>C(O)(=O)C>[Br:19][C:11]1[N:8]2[N:9]=[CH:10][C:5]([C:2]([F:1])([CH3:4])[CH3:3])=[N:6][C:7]2=[N:13][CH:12]=1

参加物

5

反応物 3

HCID 24408BromineHCID 517045Sodium AcetateHCID 222400983-(1-Fluoro-1-methylethyl)imidazo[1,2-b][1,2,4]triazine

生成物 1

HCID 11459593HCID 11459593、化合物収率 95%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒2 回

実験手順

To a stirred solution of 3-(1-fluoro-1-methylethyl)imidazo[1,2-b][1,2,4]triazine (0.6208 g, 3.45 mmol) in acetic acid (15 ml) was added sodium acetate (0.4251 g, 5.18 mmol), then, dropwise over 5 min, a solution of bromine (0.195 ml, 3.78 mmol) in acetic acid (2 ml). The solution was stirred at room temperature for 30 min, then partitioned between saturated aqueous NaHCO3 (300 ml) and ethyl acetate (150 ml). The aqueous layer (pH 7) was further extracted with ethyl acetate (2×150 ml), and the combined organic extracts were dried (Na2SO4) and evaporated in vacuo. The residue was purified by flash chromatography (silica gel, 25% EtOAc/isohexane) to afford 0.8437 g (95%) of the title compound as a yellow solid: 1H NMR (360 MHz, CDCl3) δ 1.82 (6H, d, J 22.1), 7.99 (1H, s), 8.81 (1H, d, J 1.1).

後処理

  1. custompartitioned between saturated aqueous NaHCO3 (300 ml) and ethyl acetate (150 ml)
  2. extractionThe aqueous layer (pH 7) was further extracted with ethyl acetate (2×150 ml)
  3. dry with materialthe combined organic extracts were dried (Na2SO4)
  4. customevaporated in vacuo
  5. customThe residue was purified by flash chromatography (silica gel, 25% EtOAc/isohexane)

出典と根拠

ORDレコード
ord-cb3a05a7ed7447f9a7db4388bc4ce624
出典データセット
uspto-grants-2006_02
特許番号
US07005431B2

反応ノート

読み込み中…