2-Methylimidazo[1,2-a]pyridine → 8-(1-Ethyl-propyl)-2,6-dimethyl-3-(2-methyl-imidazo[1,2-a]pyridin-3-yl)-imidazo[1,2-b]pyridazine

HRID 226052

Reaction equation

HRID 226052 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][N:5]2[CH:10]=1.[CH2:11]([CH:13]([C:16]1[C:17]2[N:18]([C:23](I)=[C:24]([CH3:26])[N:25]=2)[N:19]=[C:20]([CH3:22])[CH:21]=1)[CH2:14][CH3:15])[CH3:12]>>[CH2:11]([CH:13]([C:16]1[C:17]2[N:18]([C:23]([C:10]3[N:5]4[CH:6]=[CH:7][CH:8]=[CH:9][C:4]4=[N:3][C:2]=3[CH3:1])=[C:24]([CH3:26])[N:25]=2)[N:19]=[C:20]([CH3:22])[CH:21]=1)[CH2:14][CH3:15])[CH3:12]

Participants

3

Reactant 2

HCID 1367422-Methylimidazo[1,2-a]pyridineHCID 577526818-(1-Ethyl-propyl)-3-iodo-2,6-dimethyl-imidazo[1,2-b]pyridazine

Product 1

HCID 577526898-(1-Ethyl-propyl)-2,6-dimethyl-3-(2-methyl-imidazo[1,2-a]pyridin-3-yl)-imidazo[1,2-b]pyridazineYield 21%

Procedure

Using a procedure analogous to Example 16B, 2-methyl-imidazo[1,2-a]pyridine (Chem. Ber. 1926; 59, 2054), (0.38 g, 2.92 mmol) and 8-(1-ethyl-propyl)-3-iodo-2,6-dimethyl-imidazo[1,2-b]pyridazine (1.00 g, 2.92 mmol) give the title compound (0.21 g, 0.60 mmol, 21%). 1H NMR (CDCl3): δ 0.91 (t, J=7.5 Hz, 3H), 0.92 (t, J=7.5 Hz, 3H), 1.80-1.95 (m, 4H), 2.42 (s, 3H), 2.43 (s, 3H), 2.45 (s, 3H), 3.34-3.42 (m, 1H), 6.73 (s, 1H), 6.74 (dt, J=6.6, 0.9 Hz, 1H), 7.21-7.25 (m, 1H), 7.52 (d, J=6.6 Hz, 1H), 7.64 (d, J=6.6 Hz, 1H) ppm. ES-MS (m/z): calcd for C21H25N5 (M+H)+: 348.5. found: 348.2.

Sources & evidence

ORD record
ord-b1c6e606de2c45e280d62e360bc80aa1
Source dataset
uspto-grants-2009_07
Patent number
US07557103B2

Linked notes

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