Imidazo[1,2-a]pyridine, 2,8-dimethyl- → HCID 57752624, compound

HRID 226053Notes

Reaction equation

HRID 226053 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]2[C:9]([CH3:10])=[CH:8][CH:7]=[CH:6][N:5]2[CH:11]=1.[CH2:12]([CH:14]([C:17]1[C:18]2[N:19]([C:24](I)=[C:25]([CH3:27])[N:26]=2)[N:20]=[C:21]([CH3:23])[CH:22]=1)[CH2:15][CH3:16])[CH3:13]>>[CH3:1][C:2]1[N:3]=[C:4]2[C:9]([CH3:10])=[CH:8][CH:7]=[CH:6][N:5]2[C:11]=1[C:24]1[N:19]2[N:20]=[C:21]([CH3:23])[CH:22]=[C:17]([CH:14]([CH2:12][CH3:13])[CH2:15][CH3:16])[C:18]2=[N:26][C:25]=1[CH3:27]

Participants

3

Reactant 2

HCID 12428961Imidazo[1,2-a]pyridine, 2,8-dimethyl-HCID 577526818-(1-Ethyl-propyl)-3-iodo-2,6-dimethyl-imidazo[1,2-b]pyridazine

Product 1

HCID 57752624HCID 57752624, compoundYield 65%

Procedure

Using a procedure analogous to Example 16B, 2,8-dimethyl-imidazo[1,2-a]pyridine (J. Chem. Soc. 1951; 2411, 2415), (0.30 g, 2.06 mmol) and 8-(1-ethyl-propyl)-3-iodo-2,6-dimethyl-imidazo[1,2-b]pyridazine (0.71 g, 2.06 mmol) give the title compound (0.48 g, 1.33 mmol, 65%). 1H NMR (CDCl3): δ 0.92 (t, J=7.5 Hz, 3H), 0.93 (t, J=7.5 Hz, 3H), 1.81-1.95 (m, 4H), 2.41 (s, 3H), 2.44 (s, 3H), 2.45 (s, 3H), 2.70 (s, 3H), 3.35-3.43 (m, 1H), 6.65 (t, J=6.6 Hz, 1H0, 6.72 9s, 1H), 7.03 (d, J=6.6 Hz, 1H), 7.40 9d, J=6.6 Hz, 1) ppm. ES-MS (m/z): calcd for C22H27N5 (M+H)+: 362.5. found: 362.2.

Sources & evidence

ORD record
ord-bdd3ab05ca454998b97f6221d787a379
Source dataset
uspto-grants-2009_07
Patent number
US07557103B2

Reaction notes

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