N-Iodosuccinimide → tert-butyl 3-(3-iodo-1H-indol-5-yl)-1,2,4-thiadiazol-5-ylcarbamate

HRID 634261Notes

Reaction equation

HRID 634261 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]3[N:14]=[C:13]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[S:12][N:11]=3)=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[I:23]N1C(=O)CCC1=O.OS([O-])=O.[Na+]>C1COCC1>[I:23][C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[C:6]([C:10]3[N:14]=[C:13]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:19])([CH3:21])[CH3:20])[S:12][N:11]=3)[CH:5]=2)[NH:1][CH:2]=1

Participants

5

Reactant 3

HCID 120273N-IodosuccinimideHCID 23665763Sodium BisulfiteHCID 68356726tert-butyl 3-(1H-indol-5-yl)-1,2,4-thiadiazol-5-ylcarbamate

Product 1

HCID 68356843tert-butyl 3-(3-iodo-1H-indol-5-yl)-1,2,4-thiadiazol-5-ylcarbamateYield 58.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl (3-(1H-indol-5-yl)-1,2,4-thiadiazol-5-yl)carbamate (100 mg, 0.316 mmol) in THF (5 mL) at 0° C. was added N-iodosuccinimide (78 mg; 0.348 mmol) and the reaction was stirred for 1 h at RT. The mixture was treated with saturated aq. NaHSO3 solution (5 mL). The volatile solvent were evaporated and the crude residue was further treated with ice-cold water and petroleum ether to give tert-butyl (3-(3-iodo-1H-indol-5-yl)-1,2,4-thiadiazol-5-yl)carbamate (80 mg, 58.8%) as an off white solid. MS (ESI, pos. ion) m/z: 386.9 (M+1) (carbamic acid mass); 1H NMR (400 MHz, DMSO-d6): δ 12.42 (brs, 1H), 11.76 (brs, 1H), 8.15 (s, 1H), 8.00-7.98 (m, 1H), 7.62 (d, J=2.4 Hz, 1H), 7.49 (d, J=8.8 Hz, 1H), 1.51 (s, 9H).

Workup

  1. customThe volatile solvent were evaporated
  2. additionthe crude residue was further treated with ice-cold water and petroleum ether

Sources & evidence

ORD record
ord-261ad9a74a434a8fa199af526d763bba
Source dataset
uspto-grants-2016_04
Patent number
US09321756B2

Reaction notes

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