1-ethyl-2,3-dihydro-1H-indole-5-sulfonamide → 1-Ethylindoline-6-sulfonamide

HRID 528830Notes

Reaction equation

HRID 528830 reaction equation
C(N1C2C(=CC(S(N)(=O)=O)=CC=2)CC1)C.[C:16]([N:19]1[C:27]2[C:22](=[CH:23][CH:24]=[C:25]([S:28]([NH2:31])(=[O:30])=[O:29])[CH:26]=2)[CH2:21][CH2:20]1)(=O)[CH3:17]>>[CH2:16]([N:19]1[C:27]2[C:22](=[CH:23][CH:24]=[C:25]([S:28]([NH2:31])(=[O:29])=[O:30])[CH:26]=2)[CH2:21][CH2:20]1)[CH3:17]

Participants

3

Reactant 2

HCID 321037261-ethyl-2,3-dihydro-1H-indole-5-sulfonamideHCID 642629441H-Indole-6-sulfonamide, 1-acetyl-2,3-dihydro-2×

Product 1

HCID 867188821-Ethylindoline-6-sulfonamideYield 27%

Procedure

Following a procedure analogous to that for the synthesis of Intermediate 53, 1-acetylindoline-6-sulfonamide (Intermediate 60, 200 mg, 0.83 mmol) was converted to the title compound (50 mg, 27%) after purification using preparative HPLC. 1H NMR (CDCl3) δ 7.37 (d, J=7.5 Hz, 1H), 7.21 (d, J=9.7 Hz, 2H), 3.59 (t, J=8.1 Hz, 2H), 3.28 (q, J=8.1 Hz, 2H), 3.10 (t, J=8.1 Hz, 2H), 1.26-1.22 (m, 3H); MS(ESI+) m/z 227.1 (M+H)+.

Sources & evidence

ORD record
ord-c5fb41f6878c48b7b112981a1618bf48
Source dataset
uspto-grants-2016_05
Patent number
US09346795B2

Reaction notes

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