N-Iodosuccinimide → [1-(3-Iodo-imidazo[1,2-b]pyridazin-2-yl)-ethyl]-carbamic acid benzyl ester

HRID 2036656ノート

反応式

HRID 2036656 の反応式
[CH2:1]([O:8][C:9](=[O:22])[NH:10][CH:11]([C:13]1[N:14]=[C:15]2[CH:20]=[CH:19][CH:18]=[N:17][N:16]2[CH:21]=1)[CH3:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[I:23]N1C(=O)CCC1=O>C(#N)C.O>[CH2:1]([O:8][C:9](=[O:22])[NH:10][CH:11]([C:13]1[N:14]=[C:15]2[CH:20]=[CH:19][CH:18]=[N:17][N:16]2[C:21]=1[I:23])[CH3:12])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

5

反応物 2

HCID 120273N-IodosuccinimideHCID 67433032(1-Imidazo[1,2-b]pyridazin-2-yl-ethyl)-carbamic acid benzyl ester

生成物 1

HCID 67433097[1-(3-Iodo-imidazo[1,2-b]pyridazin-2-yl)-ethyl]-carbamic acid benzyl ester

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6342Acetonitrile溶媒

実験手順

To a solution of (1-imidazo[1,2-b]pyridazin-2-yl-ethyl)-carbamic acid benzyl ester (2.5 g, 8.44 mmol) in acetonitrile (30 mL) was added N-iodosuccinimide (2.3 g, 10.13 mmol) at rt and stirred overnight. After completion of the reaction, the mixture was diluted with water and extracted with EtOAc. The organic layer was washed with satd. sodium bicarbonate, dried over sodium sulfate, filtered and concentrated in vacuo. The crude product was purified by column chromatography using silica gel (100-200 mesh) and 0-5% MeOH in DCM to provide [1-(3-iodo-imidazo[1,2-b]pyridazin-2-yl)-ethyl]-carbamic acid benzyl ester: LC-MS (ESI) m/z 422.9 [M+H]+.

後処理

  1. customAfter completion of the reaction
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed with satd
  4. dry with materialsodium bicarbonate, dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by column chromatography

出典と根拠

ORDレコード
ord-4538b214207f46c39db986138874f505
出典データセット
uspto-grants-2013_11
特許番号
US08575183B2

反応ノート

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