1,2-Dimethoxyethane → 8-(1-Ethyl-propyl)-2,6-dimethyl-3-(1,3,5-trimethyl-1H-pyrazol-4-yl)-imidazo[1,2-b]pyridazine

HRID 1432635Notes

Reaction equation

HRID 1432635 reaction equation
I[C:2]1[N:6]2[N:7]=[C:8]([CH3:16])[CH:9]=[C:10]([CH:11]([CH2:14][CH3:15])[CH2:12][CH3:13])[C:5]2=[N:4][C:3]=1[CH3:17].[CH3:18][N:19]1[C:23]([CH3:24])=[C:22](B(O)O)[C:21]([CH3:28])=[N:20]1.C([O-])([O-])=O.[Na+].[Na+].C(COC)OC>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.O.C(O)C>[CH2:12]([CH:11]([C:10]1[C:5]2[N:6]([C:2]([C:22]3[C:21]([CH3:28])=[N:20][N:19]([CH3:18])[C:23]=3[CH3:24])=[C:3]([CH3:17])[N:4]=2)[N:7]=[C:8]([CH3:16])[CH:9]=1)[CH2:14][CH3:15])[CH3:13]

Participants

8

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 111711001,3,5-Trimethylpyrazole-4-boronic acidHCID 577526818-(1-Ethyl-propyl)-3-iodo-2,6-dimethyl-imidazo[1,2-b]pyridazine

Product 1

HCID 579331018-(1-Ethyl-propyl)-2,6-dimethyl-3-(1,3,5-trimethyl-1H-pyrazol-4-yl)-imidazo[1,2-b]pyridazineYield 6.4%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

3-Iodo-2,6-dimethyl-8-(1-ethyl-propyl)-imidazo[1,2-b]pyridazine (200 mg, 0.582 mmol), 1,3,5-trimethylpyrazole-4-boronic acid (233 mg, 1.53 mmol), Pd(PPh3)4 (13.4 mg, 0.01 mmol) are combined in a microwave pressure tube. Then 0.58 ml of 2N Na2CO3 and 3.0 ml of dimethoxyethane/H20/ethanol (7:3:2) solution is added. The mixture is microwaved at 155° C. for 20 minutes. Water is added and the mixture is extracted four times with ethyl acetate. The combined organics are dried over MgSO4, filtered, then evaporated to a residue which is chromatographed using hexanes, then 1:1 hexanes:ethyl acetate, then 100% ethyl acetate to give the title compound (6.4%) as a yellow oil. 1H-NMR (DMSO-d6): δ6.86 (s, 1H); 3.73 (s, 3H); 3.06-3.10 (m, 1H); 2.41 (s, 3H); 2.22 (s, 3H); 2.03 (s, 3H); 1.93 (s, 3H); 1.74-1.83 (m, 4H); 0.77 (t, J=7.26 Hz, 6H) ppm. MS/ES+=327 (100%, M+2).

Workup

  1. customThe mixture is microwaved at 155° C. for 20 minutes
  2. extractionthe mixture is extracted four times with ethyl acetate
  3. dry with materialThe combined organics are dried over MgSO4
  4. filtrationfiltered
  5. customevaporated to a residue which
  6. customis chromatographed

Sources & evidence

ORD record
ord-16e1350a7fce48219ef41533997008cf
Source dataset
uspto-grants-2009_11
Patent number
US07612067B2

Reaction notes

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