Ethyl Acetate → 3-Iodo-2,6-dimethyl-8-(1-propyl-butyl)-imidazo[1,2-b]pyridazine

HRID 226113Notes

Reaction equation

HRID 226113 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]2[C:9]([CH:10]([CH2:14][CH2:15][CH3:16])[CH2:11][CH2:12][CH3:13])=[CH:8][C:7]([CH3:17])=[N:6][N:5]2[CH:18]=1.C1C(=O)N([I:26])C(=O)C1.C(OCC)(=O)C>C(#N)C>[I:26][C:18]1[N:5]2[N:6]=[C:7]([CH3:17])[CH:8]=[C:9]([CH:10]([CH2:14][CH2:15][CH3:16])[CH2:11][CH2:12][CH3:13])[C:4]2=[N:3][C:2]=1[CH3:1]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 120273N-IodosuccinimideHCID 688409972,6-Dimethyl-8-(1-propyl-butyl)-imidazo[1,2-b]pyridazine

Product 1

HCID 579329063-Iodo-2,6-dimethyl-8-(1-propyl-butyl)-imidazo[1,2-b]pyridazineYield 99.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In an oven dried nitrogen purged 25 mL round bottom flask, 0.088 g (0.359 mmol) of 2,6-Dimethyl-8-(1-propyl-butyl)-imidazo[1,2-b]pyridazine, in 5 mL of dry acetonitrile is cooled to 0 C. 0.0.81 g (0.359 mmol) of NIS is added and the bath is allowed to expire. TLC in 1:1 Hexanes:Ethyl Acetate indicates SM is gone. Remove solvents to obtain 0.133 g of the title compound, quantitative yield. MS; 1H NMR (DMSO-d6)=6.985 (s, 1H); 3.262-3.190 (m, 1H); 2.502 (s, 3H); 2.480 (s, 3H); 1.823-1.600 (m, 4H); 1.182-0.985 (m, 4H); 0.804-0.768 (m, 6H) ppm.

Workup

  1. customIn an oven dried nitrogen purged 25 mL round bottom flask

Sources & evidence

ORD record
ord-a0175cd7528447278ed8a5c89a0f9fc0
Source dataset
uspto-grants-2009_07
Patent number
US07557103B2

Reaction notes

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