Benzyl Bromide → Isatin Sulfonamide 34

HRID 2191225Notes

Reaction equation

HRID 2191225 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([S:11]([N:14]3[CH2:18][CH2:17][CH2:16][C@H:15]3[CH2:19][O:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)(=[O:13])=[O:12])=[CH:8][CH:9]=2)[C:4](=[O:27])[C:3]1=[O:28].C(Br)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>>[CH2:1]([N:2]1[C:10]2[C:5](=[CH:6][C:7]([S:11]([N:14]3[CH2:18][CH2:17][CH2:16][C@H:15]3[CH2:19][O:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)(=[O:12])=[O:13])=[CH:8][CH:9]=2)[C:4](=[O:27])[C:3]1=[O:28])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

3

Reactant 2

HCID 7498Benzyl BromideHCID 52888501-Methyl-5-(2-phenoxymethyl-pyrrolidine-1-sulfonyl)-1H-indole-2,3-dione

Product 1

HCID 9847835Isatin Sulfonamide 34Yield 64%

Procedure

(S)-1-Benzyl-5-(2-phenoxymethyl-pyrrolidine-1-sulfonyl)-1H-indole-2,3-dione (2) was prepared according to the same procedure for compound 11a, except using benzyl bromide, and purified with hexanes-ether (1:2) to afford 152 mg (64%) of 2 as a yellow solid, mp 97.2-99.1° C. 1H NMR (300 MHz, CDCl3) δ 8.01 (d, J=1.5 Hz, 1H), 7.94 (dd, J=8.4 Hz, J=1.8 Hz, 1H), 7.36 (m, 5H), 7.22 (m, 2H), 6.95-6.79 (m, 4H), 4.92 (s, 2H), 4.15 (dd, J=8.85 Hz, J=2.4 Hz, 1H), 3.97-3.87 (m, 2H), 3.49 (m, 1H), 3.23 (m, 1H), 2.01 (m, 2H), 1.78 (m, 2H). Anal. Calcd for C26H24N2O5S: C, 65.53, H, 5.08; N, 5.88. Found: C, 65.27, H, 5.32; N, 5.58.

Workup

  1. custom(S)-1-Benzyl-5-(2-phenoxymethyl-pyrrolidine-1-sulfonyl)-1H-indole-2,3-dione (2) was prepared
  2. custompurified with hexanes-ether (1:2)

Sources & evidence

ORD record
ord-80986d3aeca54354b94f1b7db3655c57
Source dataset
uspto-grants-2012_12
Patent number
US08329686B2

Reaction notes

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