1-Acetylindoline-5-sulfonamide → 1-ethyl-2,3-dihydro-1H-indole-5-sulfonamide

HRID 528821

반응식

HRID 528821 반응식
[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([S:13]([NH2:16])(=[O:15])=[O:14])=[CH:10][CH:11]=2)[CH2:6][CH2:5]1)(=O)[CH3:2].B.C1COCC1>C1COCC1>[CH2:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([S:13]([NH2:16])(=[O:14])=[O:15])=[CH:10][CH:11]=2)[CH2:6][CH2:5]1)[CH3:2]

참가 물질

4

반응물 2

HCID 8042081-Acetylindoline-5-sulfonamide2회HCID 2723981Borane;tetrahydrofuran

생성물 1

HCID 321037261-ethyl-2,3-dihydro-1H-indole-5-sulfonamide수율 101.6%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a suspension of 1-acetylindoline-5-sulfonamide (Intermediate 52A, 120 mg, 0.50 mmol) in THF (2.0 mL) was added BH3.THF (5.0 mL, 5.0 mmol, 1.0M solution in THF). The resulting reaction mixture was stirred at room temperature for 1 h, then quenched carefully with MeOH and concentrated in vacuo to give the title compound (115 mg, 100%) as a white solid. 1H NMR (CD3OD) δ 7.56 (dd, J=8.4, 2.0 Hz, 1H), 7.48 (d, J=1.6 Hz, 1H), 6.46-6.44 (m, 1H), 3.51 (t, J=8.6 Hz, 2H), 3.24-3.20 (m, 2H), 2.99 (t, J=8.5 Hz, 2H), 1.17-1.13 (m, 3H); MS(ESI+) m/z 227.2 (M+H)+.

후처리

  1. customThe resulting reaction mixture
  2. customquenched carefully with MeOH
  3. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-a4461fd026ea40dfb4bae997112420eb
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09346795B2

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