N-bromobutanimide → HCID 86701680, compound

HRID 2174057Notes

Reaction equation

HRID 2174057 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH3:27])[C:5]([C:21]#[C:22][Si](C)(C)C)=[C:6]2[C:10]=1[N:9]([S:11]([C:14]1[CH:20]=[CH:19][C:17]([CH3:18])=[CH:16][CH:15]=1)(=[O:13])=[O:12])[CH:8]=[CH:7]2.C1C(=O)N([Br:35])C(=O)C1>CC(C)=O.[N+]([O-])([O-])=O.[Ag+]>[Br:1][C:2]1[CH:3]=[C:4]([CH3:27])[C:5]([C:21]#[C:22][Br:35])=[C:6]2[C:10]=1[N:9]([S:11]([C:14]1[CH:20]=[CH:19][C:17]([CH3:18])=[CH:16][CH:15]=1)(=[O:13])=[O:12])[CH:8]=[CH:7]2

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 86701678HCID 86701678, compound

Product 1

HCID 86701680HCID 86701680, compound

Reagents, catalysts & solvents 2

HCID 24470Silver NitrateCatalystHCID 180AcetoneSolvent2×

Procedure

To a suspension of 7-bromo-5-methyl-1-tosyl-4-((trimethylsilyl)ethynyl)-1H-indole (70 mg, 0.152 mmol) and AgNO3 (7.75 mg, 0.046 mmol) in acetone (0.8 mL) at 0° C. was added a solution of NBS (38 mg, 0.213 mmol) in acetone (0.8 mL) and the mixture was warmed to room temperature. After stirring overnight the reaction was purified directly by flash chromatography (0-40% EtOAc in heptanes) to provide the title compound. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.03 (d, J=3.79 Hz, 1H) 7.72 (d, J=8.59 Hz, 2H) 7.37-7.48 (m, 3H) 6.91 (d, J=3.79 Hz, 1H) 2.38 (s, 3H) 2.37 (s, 3H).

Workup

  1. customwas purified directly by flash chromatography (0-40% EtOAc in heptanes)

Sources & evidence

ORD record
ord-5e04cbfe3a324f6d9789d2c2b2aa7585
Source dataset
uspto-grants-2015_06
Patent number
US09056874B2

Reaction notes

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