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3-[8-(1-Ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazin-3-yl]-2-methyl-imidazo[1,2-a]pyridine-8-carboxaldehyde → 1-{3-[8-(1-Ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazin-3-yl]-2-methyl-imidazo[1,2-a]pyridin-8-yl}-ethanol

HRID 226049
Notes
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Reaction equation

HRID 226049 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].[CH3:29][Mg+].[Br-]>C1COCC1>[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])[CH3:29])[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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 577525973-[8-(1-Ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazin-3-yl]-2-methyl-imidazo[1,2-a]pyridine-8-carboxaldehydeHCID 178418689HCID 178418689, compound

Product 1

HCID 577527071-{3-[8-(1-Ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazin-3-yl]-2-methyl-imidazo[1,2-a]pyridin-8-yl}-ethanolYield 83.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 3-[8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazin-3-yl]-2-methyl-imidazo[1,2-a]pyridine-8-carboxaldehyde (1.07 g, 2.84 mmol) in THF (30 mL) is cooled at 0° C., treated with 3.0 M CH3MgBr (1.1 mL, 3.41 mmol). The reaction is stirred at 0° C. for 30 min. It is then quenched with sat. NH4Cl (15 mL), diluted with H2O (15 mL), extracted with EtOAc (2×30 mL). The combined organic layers is dried with Na2SO4, filtered and concentrated. Purification of the crude material by silica gel chromatography gives the title compound (0.93 g, 2.38 mmol, 83). 1H NMR (CDCl3): δ 0.91 (t, J=7.1 Hz, 3H), 0.92 (t, J=7.1 Hz, 3H), 1.75 (d, J=6.6 Hz, 3H), 1.79-1.94 (m, 4H), 2.41 (s, 6H), 2.45 (s, 3H), 3.32-3.42 (m, 1H), 5.17 (m, 1H), 5.39 (m, 1H), 6.72 (t, J=7.0 Hz, 1H), 6.73 (s, 1H), 7.13 (d, J=7.1 Hz, 1H), 7.43 (d, J=7.1 Hz, 1H) ppm. ES-MS (m/z): calcd for C23H29N5O (M+H)+: 392.5. found: 392.3.

Workup

  1. customIt is then quenched with sat. NH4Cl (15 mL)
  2. additiondiluted with H2O (15 mL)
  3. extractionextracted with EtOAc (2×30 mL)
  4. dry with materialThe combined organic layers is dried with Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification of the crude material by silica gel chromatography

Sources & evidence

ORD record
ord-25330e68c0f548f78a0a088520a6834e
Source dataset
uspto-grants-2009_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07557103B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes