Trifluoromethanesulfonic anhydride → 6-chloro-4-(4-fluoro-1H-indol-2-yl)pyridin-3-yl trifluoromethanesulfonate

HRID 595673ノート

反応式

HRID 595673 の反応式
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([OH:8])=[C:4]([C:9]2[NH:10][C:11]3[C:16]([CH:17]=2)=[C:15]([F:18])[CH:14]=[CH:13][CH:12]=3)[CH:3]=1.CCN(C(C)C)C(C)C.[O:28](S(C(F)(F)F)(=O)=O)[S:29]([C:32]([F:35])([F:34])[F:33])(=O)=[O:30]>CN(C1C=CN=CC=1)C.C(Cl)Cl.O>[F:33][C:32]([F:35])([F:34])[S:29]([O:8][C:5]1[CH:6]=[N:7][C:2]([Cl:1])=[CH:3][C:4]=1[C:9]1[NH:10][C:11]2[C:16]([CH:17]=1)=[C:15]([F:18])[CH:14]=[CH:13][CH:12]=2)(=[O:30])=[O:28]

参加物

7

反応物 3

HCID 67749Trifluoromethanesulfonic anhydrideHCID 81531DiisopropylethylamineHCID 903339356-chloro-4-(4-fluoro-1H-indol-2-yl)pyridin-3-ol

生成物 1

HCID 903335056-chloro-4-(4-fluoro-1H-indol-2-yl)pyridin-3-yl trifluoromethanesulfonate収率 80%

試薬・触媒・溶媒 3

HCID 142844-(Dimethylamino)pyridine触媒HCID 962Water溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
25 °C

実験手順

To a solution of 6-chloro-4-(4-fluoro-1H-indol-2-yl)pyridin-3-ol (prepared using similar method described in Example 1, 500 mg, 1.9 mmol), DIPEA (490 mg, 3.8 mmol) and DMAP (5 mg, 0.02 mmol) in DCM (2 mL) was added Tf2O (1.07 g, 3.8 mmol) dropwise at 0° C. under nitrogen. The mixture was stirred at 25° C. for 5 hours. The mixture was diluted with H2O extracted with EtOAc, then the combined organic phase was washed with brine, dried over Na2SO4 and concentrated in vacuo to give the crude product. It was purified by column (PE:EA=5:1) to obtain the product of 6-chloro-4-(4-fluoro-1H-indol-2-yl)pyridin-3-yl trifluoromethanesulfonate (600 mg, yield: 80%). 1H-NMR (CDCl3, 400 MHz) δ 8.71 (s, 1H), 8.39 (s, 1H), 7.64 (s, 1H), 7.18˜7.20 (m, 3H), 6.77˜6.82 (m, 1H). MS (M+H)+: 395/397.

後処理

  1. extractionextracted with EtOAc
  2. washthe combined organic phase was washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customto give the crude product
  6. customIt was purified by column (PE:EA=5:1)

出典と根拠

ORDレコード
ord-0dfc593eb76d4ea298d2fe1795376fb7
出典データセット
uspto-grants-2016_01
特許番号
US09243002B2

反応ノート

読み込み中…