N-Iodosuccinamide → HCID 68825648, compound

HRID 230759Notes

Reaction equation

HRID 230759 reaction equation
[I:1]NC(=O)CCC(N)=O.[NH:10]1[C:18]2[CH:17]=[CH:16][N:15]=[C:14]([NH:19][C:20](=[O:24])[O:21][CH2:22][CH3:23])[C:13]=2[CH:12]=[CH:11]1>C1COCC1>[I:1][C:12]1[C:13]2[C:14]([NH:19][C:20](=[O:24])[O:21][CH2:22][CH3:23])=[N:15][CH:16]=[CH:17][C:18]=2[NH:10][CH:11]=1

Participants

4

Reactant 2

HCID 21864724N-IodosuccinamideHCID 68827324HCID 68827324, compound

Product 1

HCID 68825648HCID 68825648, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-Iodosuccinamide (0.030 g, 0.13 mmol, 1.0 eq) was added to a solution of ethyl 1H-pyrrolo[3,2-c]pyridin4-ylcarbamate (0.027 g, 0.13 mmol, 1.0 eq) in THF (1 mL) at room temperature and the reaction mixture was stirred for 15 minutes. The reaction mixture was quenched with 10% NaHSO3 solution and extracted with 10/1 CHCl3/MeOH. The combined organic extracts were dried (Na2SO4), filtered and concentrated in vacuo. The residue was purified by flash chromatography (SiO2, eluting 0-5% CHCl3/MeOH) to afford the product (0.031 g, 72%) as a solid. 1H NMR (CD3OD) δ 7.87 (d, 1H, J=5.9 Hz), 7.38 (s, 1H), 7.25 ((d, 1H, J=5.9 Hz), 4.14 (q, 2H, J=7.1 Hz), 1.12 (t, 3H, J=7.1 Hz); MS(ESI+) m/z 332 (M+H)+. Calculated: 331.9896, found: 331.9884.

Workup

  1. customThe reaction mixture was quenched with 10% NaHSO3 solution
  2. extractionextracted with 10/1 CHCl3/MeOH
  3. dry with materialThe combined organic extracts were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography (SiO2, eluting 0-5% CHCl3/MeOH)

Sources & evidence

ORD record
ord-860dc91cc27a4ada811af96293f21ffb
Source dataset
uspto-grants-2009_07
Patent number
US07566784B2

Reaction notes

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