N-Iodosuccinimide → HCID 178455023、化合物

HRID 1053634

反応式

HRID 1053634 の反応式
[Si:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][N:13]=[CH:12]2)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C1C(=O)N([I:25])C(=O)C1>CN(C)C=O>[Si:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][N:13]=[C:12]2[I:25])([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2]

参加物

4

反応物 2

HCID 120273N-IodosuccinimideHCID 580425115-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]-1H-indazole

生成物 1

HCID 178455023HCID 178455023、化合物収率 98%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 5-[(tert-butyldimethylsilyl)oxy]-1H-indazole (13 g, 52.34 mmol, 1.00 equiv) in N,N-dimethylformamide (550 mL) maintained under nitrogen was added NIS (28.6 g, 104.76 mmol, 2.00 equiv) in portions. The reaction mixture was stirred at room temperature overnight and then concentrated under vacuum. The residue was purified on a silica gel column eluted with 0-10% of ethyl acetate in petroleum ether to give 19.2 g (98%) of 5-(tert-butyldimethylsilyloxy)-3-iodo-1H-indazole as an off-white solid. 1H NMR (300 MHz, CDCl3): δ 7.50-7.45 (m, 1H), 7.09 (dd, J=9.0 Hz, 2.1 Hz, 1H), 6.98-6.70 (m, 1H), 1.10 (s, 9H), 0.24 (s, 6H) ppm. LCMS (method A, ESI): RT=1.80 min, m/z=374.9 [M+H]+.

後処理

  1. concentrationconcentrated under vacuum
  2. customThe residue was purified on a silica gel column
  3. washeluted with 0-10% of ethyl acetate in petroleum ether

出典と根拠

ORDレコード
ord-eb793d94eabb4d009c81ff497987b181
出典データセット
uspto-grants-2016_07
特許番号
US09394258B2

関連ノート

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