HCID 57752597, compound → HCID 68857867, compound

HRID 226103Notes

Reaction equation

[CH2:1]([CH:3]([C:6]1[C:7]2[N:8]([C:13]([C:17]3[N:21]4[CH:22]=[CH:23][CH:24]=[C:25]([CH:26]=[O:27])[C:20]4=[N:19][C:18]=3[CH3:28])=[C:14]([CH3:16])[N:15]=2)[N:9]=[C:10]([CH3:12])[CH:11]=1)[CH2:4][CH3:5])[CH3:2].[C:29]([Mg]Br)([CH3:32])([CH3:31])[CH3:30]>>[CH2:1]([CH:3]([C:6]1[C:7]2[N:8]([C:13]([C:17]3[N:21]4[CH:22]=[CH:23][CH:24]=[C:25]([CH:26]([OH:27])[C:29]([CH3:32])([CH3:31])[CH3:30])[C:20]4=[N:19][C:18]=3[CH3:28])=[C:14]([CH3:16])[N:15]=2)[N:9]=[C:10]([CH3:12])[CH:11]=1)[CH2:4][CH3:5])[CH3:2]

Participants

Reactant 2

HCID 57752597HCID 57752597, compound

HCID 178418586HCID 178418586, compound

Product 1

HCID 68857867HCID 68857867, compoundYield 66%

Procedure

Using a procedure analogous to Example 41, 3-[8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazin-3-yl]-2-methyl-imidazo[1,2-a]pyridine-8-carbaldehyde (0.20 g, 0.53 mmol) and t-BuMgBr (2.0 M, 0.32 mL, 0.64 mmol) give the title compound (91.9 mg, 0.21 mmol, 66%). 1H NMR (CDCl3): δ 0.87-0.95 (m, 6H), 1.06 (s, 4.5H), 1.07 (s, 4.5H), 1.79-1.94 (m, 4H), 2.38 (s, 3H), 2.42 (s, 3H), 2.46 (s, 3H), 3.30-3.41 (m, 1H), 4.65-5.80 (m, 1H), 6.69-6.76 (m, 2H), 7.05 (bs, 1H), 7.43 (dd, J=13.7, 7.1 Hz, 1H) ppm. ES-MS (m/z): calcd for C26H35N5O (M+1)+: 434.6. found: 434.5.

Sources & evidence

ORD record: ord-5324eb3a244042dd8cd1c56e3f0c2246
Source dataset: uspto-grants-2009_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07557103B2

Reaction notes

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