Sodium Carbonate → HCID 57933069, compound

HRID 1432571Notes

Reaction equation

HRID 1432571 reaction equation
[CH3:1][C:2]1[C:3](B(O)O)=[CH:4][S:5][CH:6]=1.[CH2:10]([CH:12]([C:15]1[C:16]2[N:17]([C:22](I)=[C:23]([CH3:25])[N:24]=2)[N:18]=[C:19]([CH3:21])[CH:20]=1)[CH2:13][CH3:14])[CH3:11].C([O-])([O-])=O.[Na+].[Na+]>O.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>[CH2:10]([CH:12]([C:15]1[C:16]2[N:17]([C:22]([C:3]3[C:2]([CH3:1])=[CH:6][S:5][CH:4]=3)=[C:23]([CH3:25])[N:24]=2)[N:18]=[C:19]([CH3:21])[CH:20]=1)[CH2:13][CH3:14])[CH3:11]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 50839314-Methyl-3-thiopheneboronic acidHCID 577526818-(1-Ethyl-propyl)-3-iodo-2,6-dimethyl-imidazo[1,2-b]pyridazine

Product 1

HCID 57933069HCID 57933069, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Procedure

To a 100 mL round bottom flask containing 4-methyl 3-thiophene boronic acid (0.27 g, 1.91 mmol), and 8-(1-ethyl-propyl)-3-iodo-2,6-dimethyl-imidazo[1,2-b]pyridazine (0.65 g, 1.91 mmol) in 20 mL of a stock solution (DME:H2O:EtOH=7:3:2) is added 2 M Na2CO3 (1.9 mL). The resulting mixture is degassed by bubbling N2 for 5 min. Then Pd(PPh3)4 (0.11 g, 0.096 mmol) is added. The reaction mixture is refluxed overnight. The reaction is diluted with H2O (20 mL); extracted with EtOAc (3×30 mL); dried (Na2SO4), filtered and purification of the crude material by chromatography gives the title compound (0.52 g, 1.66 mmol, 87%). 1H NMR (CDCl3): δ 0.89 (t, J=7.5 Hz, 6H), 1.75-1.90 (m, 4H), 2.13 (d, J=0.8 Hz, 3H), 2.44 (s, 3H), 2.49 (s, 3H), 3.30-3.39 (m, 1H), 6.64 (s, 1H), 7.08-7.11 (m, 1H), 7.34 (d, J=3.1 Hz, 1H). ES-MS (m/z): calcd for C18H23N3S (M+H)+: 314.5; found: 314.2.

Workup

  1. customThe resulting mixture is degassed
  2. customby bubbling N2 for 5 min
  3. temperatureThe reaction mixture is refluxed overnight
  4. extractionextracted with EtOAc (3×30 mL)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. custompurification of the crude material by chromatography

Sources & evidence

ORD record
ord-0b54588b4cf545a3b427defe6d06ff1a
Source dataset
uspto-grants-2009_11
Patent number
US07612067B2

Reaction notes

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