N-Iodosuccinimide → 2-(2-Chlorophenyl)-3-(4-chlorophenyl)-7-iodomethyl-6,7-dihydro-8-oxa-1,4,8b-triaza-as-indacene

HRID 348037ノート

反応式

HRID 348037 の反応式
[CH2:1]([C:4]1[CH:5]=[N:6][C:7]2[N:8]([N:11]=[C:12]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[Cl:27])[C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)[C:9]=1[OH:10])[CH:2]=[CH2:3].[I:28]N1C(=O)CCC1=O>C(Cl)Cl.C(Cl)(Cl)Cl>[Cl:27][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=1[C:12]1[C:13]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)=[C:7]2[N:8]([C:9]3[O:10][CH:2]([CH2:3][I:28])[CH2:1][C:4]=3[CH:5]=[N:6]2)[N:11]=1

参加物

4

反応物 2

HCID 120273N-IodosuccinimideHCID 178439549HCID 178439549、化合物

生成物 1

HCID 100069482-(2-Chlorophenyl)-3-(4-chlorophenyl)-7-iodomethyl-6,7-dihydro-8-oxa-1,4,8b-triaza-as-indacene

試薬・触媒・溶媒 1

HCID 18399249Chloroform dichloromethane溶媒

実験手順

To a mixture of 6-allyl-3-(4-chlorophenyl)-2-(2-chlorophenyl)-pyrazolo[1,5-a]pyrimidin-7-ol (I-15A-1a; 25 mg, 0.063 mmol) in 9:1 methylene chloride/chloroform (0.63 ml) at 0° C. was added N-iodosuccinimide (15 mg, 0.066 mmol), portionwise. The reaction was stirred overnight at room temperature and then extracted from water with ethyl acetate. The combined organic layers were washed with brine, dried (MgSO4), and then concentrated, in vacuo. Purification on a Biotage™ Flash 12S column using 20% ethyl acetate in hexanes as eluant afforded compound 15A-1 (15 mg, 46%) as a solid: +ESI MS (M+1) 522.3; 1H NMR (400 MHz, CD3OD) δ 8.46 (s, 1H), 7.53–7.40 (m, 6H), 7.24 (d, J=8.7 Hz, 2H), 5.45–5.41 (m, 1H), 3.81–3.64 (m, 2H), 3.33 (d, J=6.2 Hz, 2H).

後処理

  1. extractionextracted from water with ethyl acetate
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated, in vacuo
  5. customPurification on a Biotage™ Flash 12S column
  6. customafforded compound 15A-1 (15 mg, 46%) as a solid

出典と根拠

ORDレコード
ord-45c210288c4843b49c840a060e68abf2
出典データセット
uspto-grants-2007_02
特許番号
US07176210B2

反応ノート

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