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

HRID 595673노트

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HRID 595673 반응식
[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]

참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 142844-(Dimethylamino)pyridine촉매HCID 962Water용매HCID 6344Dichloromethane용매

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온도
25 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-0dfc593eb76d4ea298d2fe1795376fb7
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09243002B2

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