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

HRID 528821Notes

Reaction equation

HRID 528821 reaction equation
[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]

Participants

4

Reactant 2

HCID 8042081-Acetylindoline-5-sulfonamide2×HCID 2723981Borane;tetrahydrofuran

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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)+.

Workup

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

Sources & evidence

ORD record
ord-a4461fd026ea40dfb4bae997112420eb
Source dataset
uspto-grants-2016_05
Patent number
US09346795B2

Reaction notes

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