N-Iodosuccinimide → HCID 59277781, compound

HRID 341213Notes

Reaction equation

HRID 341213 reaction equation
[I:1]N1C(=O)CCC1=O.[CH3:9][N:10]1[N:14]=[N:13][C:12]([C:15]2[CH:20]=[CH:19][N:18]3[CH:21]=[CH:22][N:23]=[C:17]3[CH:16]=2)=[N:11]1>CN(C=O)C>[I:1][C:21]1[N:18]2[CH:19]=[CH:20][C:15]([C:12]3[N:13]=[N:14][N:10]([CH3:9])[N:11]=3)=[CH:16][C:17]2=[N:23][CH:22]=1

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 59277808HCID 59277808, compound

Product 1

HCID 59277781HCID 59277781, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-Iodo succinimide (300 mg, 1.3 mmol) was added in one portion to a stirred suspension of 7-(2-methyl-2H-tetrazol-5-yl)-imidazo[1,2-a]pyridine (240 mg, 1.2 mmol) in dry DMF (2 ml) at RT under N2. After 5 hours, the reaction was quenched with saturated aqueous sodium thiosulphate/saturated aqueous NaHCO3 (1:1, 2 ml). Water (2 ml) was then added and the mixture was stirred at RT for 15 minutes. The solid was collected by filtration and dried in vacuo to give the title compound (360 mg) as a cream solid. 1H NMR (400 MHz, DMSO-d6): 8.51 (1H, dd), 8.20 (1H, dd), 7.86 (1H, s), 7.65 (1H, dd), 4.47 (3H, s).

Workup

  1. customthe reaction was quenched with saturated aqueous sodium thiosulphate/saturated aqueous NaHCO3 (1:1, 2 ml)
  2. additionWater (2 ml) was then added
  3. filtrationThe solid was collected by filtration
  4. customdried in vacuo

Sources & evidence

ORD record
ord-d3ffaf34be314a609b28f44bd82fef3b
Source dataset
uspto-grants-2014_11
Patent number
US08895745B2

Reaction notes

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