Sodium Carbonate → 2,6-Dimethyl-8-(1-propyl-butyl)-3-(1,3,5-trimethyl-1H-pyrazol-4-yl)-imidazo[1,2-b]pyridazine

HRID 1432636Notes

Reaction equation

HRID 1432636 reaction equation
I[C:2]1[N:6]2[N:7]=[C:8]([CH3:18])[CH:9]=[C:10]([CH:11]([CH2:15][CH2:16][CH3:17])[CH2:12][CH2:13][CH3:14])[C:5]2=[N:4][C:3]=1[CH3:19].[CH3:20][N:21]1[C:25]([CH3:26])=[C:24](B(O)O)[C:23]([CH3:30])=[N:22]1.C([O-])([O-])=O.[Na+].[Na+].COC.O.C(O)C>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:19][C:3]1[N:4]=[C:5]2[C:10]([CH:11]([CH2:15][CH2:16][CH3:17])[CH2:12][CH2:13][CH3:14])=[CH:9][C:8]([CH3:18])=[N:7][N:6]2[C:2]=1[C:24]1[C:23]([CH3:30])=[N:22][N:21]([CH3:20])[C:25]=1[CH3:26]

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 111711001,3,5-Trimethylpyrazole-4-boronic acidHCID 579329063-Iodo-2,6-dimethyl-8-(1-propyl-butyl)-imidazo[1,2-b]pyridazineHCID 86620092Dimethyl ether water ethanol

Product 1

HCID 579329602,6-Dimethyl-8-(1-propyl-butyl)-3-(1,3,5-trimethyl-1H-pyrazol-4-yl)-imidazo[1,2-b]pyridazineYield 22.8%

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

3-Iodo-2,6-dimethyl-8-(1-propyl-butyl)-imidazo[1,2-b]pyridazine (75 mg, 0.20 mmol), 1,3,5-trimethylpyrazole-4-boronic acid (80 mg, 0.52 mmol), 2N Na2CO3 solution (0.22 ml), and 5.0 mg (0.0004 mmol) of Pd(PPh3)4 are combined in microwave pressure vessel with 1.5 ml of dimethylether/H2O/ethanol (7:3:2) solution. The mixture is microwaved at 140° C. for 25 minutes. The mixture is evaporated and chromatographed on silica gel column using hexanes then 3:1 hexane:ethyl acetate, then 1:1 hexane:ethyl acetate to give the title compound (22.8%) as a clear oil. 1H-NMR (DMSO-d6): δ6.88 (s, 1H); 3.72 (s, 3H); 3.06-3.10 (m, 1H); 2.40 (s, 3H); 2.21 (s, 3H); 2.02 (s, 3H); 1.92 (s, 3H); 1.60-1.76 (m, 4H); 1.08-1.21 (m, 4H); 0.82 (t, J=7.49 Hz, 6H) ppm. MS/ES+354 (100%, M+1).

Workup

  1. customThe mixture is microwaved at 140° C. for 25 minutes
  2. customThe mixture is evaporated
  3. customchromatographed on silica gel column

Sources & evidence

ORD record
ord-06e428a745174f7aab629c14fab4078a
Source dataset
uspto-grants-2009_11
Patent number
US07612067B2

Reaction notes

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