4-Toluenesulfonyl chloride → 6-Fluoro-1-tosylindoline

HRID 56068

反応式

HRID 56068 の反応式
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[F:12][C:13]1[CH:21]=[C:20]2[C:16]([CH2:17][CH2:18][NH:19]2)=[CH:15][CH:14]=1.[NH4+].[Cl-]>C1COCC1.N1C=CC=CC=1>[F:12][C:13]1[CH:21]=[C:20]2[C:16]([CH2:17][CH2:18][N:19]2[S:7]([C:4]2[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=2)(=[O:9])=[O:8])=[CH:15][CH:14]=1

参加物

6

反応物 3

HCID 73974-Toluenesulfonyl chlorideHCID 25517Ammonium ChlorideHCID 2604006-fluoro-2,3-dihydro-1H-indole

生成物 1

HCID 606033976-Fluoro-1-tosylindoline収率 61.2%

試薬・触媒・溶媒 2

HCID 1049Pyridine溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

4-Toluenesulfonyl chloride (460 mg, 2.4 mmol) was slowly added to a solution of 6-fluoro-2,3-dihydro-1H-indole (220 mg, 1.6 mmol) in THF (6 mL) and pyridine (260 μL). The reaction mixture was stirred at room temperature overnight. Upon the completion of the reaction, the mixture was cooled to 0° C., neutralized with aq. sat. NH4Cl (10 mL) and extracted with EtOAc (3×10 mL). The combined extracts were sequentially washed with aq. sat. NH4Cl (3×10 mL), brine (10 mL) and dried (MgSO4). The crude product was concentrated and dried over high vacuum. Chromatography of the residue (EtOAc/hexanes=1/3) gave 283 mg (0.98 mmol) of the title product. Yield: 61%, colorless oil. 1H NMR (300 MHz, CDCl3): δ 7.67 (d, J=8.2 Hz, 2H), 7.35 (dd, J=10.0, 2.3 Hz, 1H), 7.23 (d, J=8.2 Hz, 2H), 6.97 (m, 1H), 6.62 (m, 1H), 3.90 (t, J=8.4 Hz, 2H), 2.84 (t, J=8.4 Hz, 2H), 2.35 (s, 3H) ppm. 13C NMR (75 MHz, CDCl3): δ 162.5 (d, J=241.4 Hz), 144.5, 143.3 (d, J=11.7 Hz), 133.6, 129.8, 127.2, 127.0 (d, J=2.6 Hz), 125.7 (d, J=9.8 Hz), 110.0 (d, J=22.6 Hz), 102.8 (d, J=28.4 Hz), 50.7, 27.1, 21.5 ppm.

後処理

  1. customUpon the completion of the reaction
  2. temperaturethe mixture was cooled to 0° C.
  3. extractionextracted with EtOAc (3×10 mL)
  4. washThe combined extracts were sequentially washed with aq. sat. NH4Cl (3×10 mL), brine (10 mL)
  5. dry with materialdried (MgSO4)
  6. concentrationThe crude product was concentrated
  7. customdried over high vacuum

出典と根拠

ORDレコード
ord-3bbb81c43f5643c897226bdd9bb9b9fe
出典データセット
uspto-grants-2016_09
特許番号
US09434699B2

関連ノート

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