Trifluoroacetic acid → HCID 54589123, compound

HRID 2284369Notes

Reaction equation

HRID 2284369 reaction equation
I[C:2]1[N:6]2[N:7]=[CH:8][CH:9]=[C:10]([C:11]3[CH:12]=[N:13][CH:14]=[CH:15][C:16]=3[CH3:17])[C:5]2=[N:4][CH:3]=1.C(O)(C(F)(F)F)=O.C([Sn](CCCC)(CCCC)[C:30]1[CH:35]=[N:34][CH:33]=[CH:32][N:31]=1)CCC>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.O1CCOCC1>[CH3:17][C:16]1[CH:15]=[CH:14][N:13]=[CH:12][C:11]=1[C:10]1[C:5]2[N:6]([C:2]([C:30]3[CH:35]=[N:34][CH:33]=[CH:32][N:31]=3)=[CH:3][N:4]=2)[N:7]=[CH:8][CH:9]=1

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 27373162-(Tributylstannyl)pyrazineHCID 67466328HCID 67466328, compound

Product 1

HCID 54589123HCID 54589123, compoundYield 30%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

A microwave vial was charged with a mixture of 3-iodo-8-(4-methylpyridin-3-yl)imidazo[1,2-b]pyridazine, TFA (66 mg, 0.147 mmol), 2-(tributylstannyl)pyrazine (162 mg, 0.440 mmol), tetrakis(triphenylphosphine)palladium(0) (33.9 mg, 0.029 mmol), and dioxane (4 mL) was stirred at RT for 5 min. under nitrogen. The resulting mixture was heated to 114° C. for 15 h in microwave. The reaction mixture was cooled to room temperature and concentrated under reduced pressure. The residue was purified by prep. HPLC to give 18.2 mg (30%) product. 1H NMR (400 MHz, CD3OD) δ ppm 9.86 (1H, d, J=1.76 Hz), 8.97 (1H, s), 8.86 (2H, dd, J=16.12, 5.29 Hz), 8.66-8.79 (1H, m), 8.59 (1H, d, J=2.52 Hz), 8.56 (1H, s), 8.10 (1H, d, J=6.04 Hz), 7.54 (1H, d, J=4.78 Hz), 2.57 (3H, s); LC (Conditions B & C): >95% purity. LC/MS: Rt=1.05 min. LC/MS (Condition A): 289.12.

Workup

  1. temperatureThe resulting mixture was heated to 114° C. for 15 h in microwave
  2. temperatureThe reaction mixture was cooled to room temperature
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by prep

Sources & evidence

ORD record
ord-14f1bc557edb42538a76efaa923f8810
Source dataset
uspto-grants-2015_09
Patent number
US09145419B2

Reaction notes

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