N-Iodosuccinimide → HCID 11374420, compound

HRID 2356247Notes

Reaction equation

HRID 2356247 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[N:13]=[C:14]3[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][CH3:23])=[N:16][N:15]3[CH:24]=2)=[CH:8][CH:7]=1.[I:25]N1C(=O)CCC1=O>C(#N)C>[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[N:13]=[C:14]3[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][CH3:23])=[N:16][N:15]3[C:24]=2[I:25])=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 11381836HCID 11381836, compound

Product 1

HCID 11374420HCID 11374420, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 2-[4-(2-methoxyethoxy)phenyl]-6-propoxyimidazo[1,2-b]pyridazine (327 mg, 1.00 mmol), N-iodosuccinimide (225 mg, 1.00 mmol) and acetonitrile (4 mL) was stirred at room temperature for 1.5 hours. The mixture was filtered and the collected solid washed with cold, fresh acetonitrile to afforded Compound 96 (344 mg, 76%) as an off-white solid. 1H n.m.r. (CDCl3) δ 1.08, t, J=7.3 Hz, 3H; 1.8-2.0, m, 2H; 3.47, s, 3H; 3.75-3.83, m, 2H; 4.15-4.23, m, 2H; 4.41, t, J=6.6 Hz, 2H; 6.76, d, J=9.5 Hz, 1H; 7.04, d, J=9.3 Hz, 2H; 7.80, d, J=9.9 Hz, 1H; 8.04, d, J=8.7 Hz, 2H. Mass spectrum (APCI+) m/z 454 (M+H, 100%).

Workup

  1. filtrationThe mixture was filtered
  2. washthe collected solid washed with cold, fresh acetonitrile

Sources & evidence

ORD record
ord-a3d6fcf858674e0f8fb10d890e886c91
Source dataset
uspto-grants-2010_07
Patent number
US07759349B2

Reaction notes

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