N-Iodosuccinimide → HCID 178520933、化合物

HRID 550097ノート

反応式

HRID 550097 の反応式
[Cl:1][C:2]1[C:3]2[N:4]([C:8]([C@H:11]3[CH2:16][CH2:15][C@H:14]([CH2:17][OH:18])[CH2:13][CH2:12]3)=[N:9][CH:10]=2)[CH:5]=[CH:6][N:7]=1.[I:19]N1C(=O)CCC1=O>CN(C=O)C.C(Cl)Cl>[Cl:1][C:2]1[C:3]2[N:4]([C:8]([C@H:11]3[CH2:12][CH2:13][C@H:14]([CH2:17][OH:18])[CH2:15][CH2:16]3)=[N:9][C:10]=2[I:19])[CH:5]=[CH:6][N:7]=1

参加物

5

反応物 2

HCID 120273N-IodosuccinimideHCID 178520932HCID 178520932、化合物

生成物 1

HCID 178520933HCID 178520933、化合物

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

実験手順

trans-[4-(8-Chloroimidazo[1,5-a]pyrazin-3-yl)cyclohexyl]methanol (18.00 g, 67.74 mmol) and N-iodosuccinimide (19.81 g, 88.06 mmol) in anhydrous DMF (360 mL) were stirred at 60° C. under N2 for 6 h. The reaction was diluted with DCM (-600 mL), washed with water and brine, dried over anhydrous Na2SO4 and then concentrated in vacuo. The crude material was purified by a silica gel flash chromatography (eluted with 1:2 EtOAc/DCM to 1:1 EtOAcIDCM) to obtain the desired product as a pale yellow solid; By 1H NMR analysis, the product was contaminated with 0.35 eq. of NIS-impurity. The product was carried onto the next reaction without further purification; MS (ES+): m/z 391.92 (100) [MH+], 393.88 (50) [MH+2], 394.89 (10) [MH+3]; tR(polar-5 min/openlynx) 2.79 min.

後処理

  1. washwashed with water and brine
  2. dry with materialdried over anhydrous Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe crude material was purified by a silica gel flash chromatography (eluted with 1:2 EtOAc/DCM to 1:1 EtOAcIDCM)

出典と根拠

ORDレコード
ord-dc9bb9419f8841f984440d2d87cdf4c1
出典データセット
uspto-grants-2011_05
特許番号
US07943767B2

反応ノート

読み込み中…