Triethylamine → HCID 58046440, compound

HRID 2046407Notes

Reaction equation

HRID 2046407 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7](Br)=[C:8]([C:10]2[N:14]3[N:15]=[CH:16][CH:17]=[CH:18][C:13]3=[N:12][CH:11]=2)[CH:9]=1)=[O:4].[CH:20]([B-](F)(F)F)=[CH2:21].[K+].C(N(CC)CC)C>C(O)CC.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(Cl)Cl>[CH:20]([C:7]1[S:6][C:5]([C:3]([O:2][CH3:1])=[O:4])=[CH:9][C:8]=1[C:10]1[N:14]2[N:15]=[CH:16][CH:17]=[CH:18][C:13]2=[N:12][CH:11]=1)=[CH2:21]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 23679353Potassium vinyltrifluoroborateHCID 58046405Methyl 5-bromo-4-(imidazo[1,2-b]pyridazin-3-yl)thiophene-2-carboxylate

Product 1

HCID 58046440HCID 58046440, compound

Reagents, catalysts & solvents 2

HCID 178418807HCID 178418807, compoundCatalystHCID 10311-PropanolSolvent

Conditions

Temperature
100 °C

Procedure

Methyl-5-bromo-4-(imidazo[1,2-b]pyridazin-3-yl)thiophene-2-carboxylate (200 mg, 0.591 mmol), potassium vinyltrifluoroborate (119 mg, 0.887 mmol), PdCl2(dppf)-CH2Cl2 adduct (48 mg, 0.059 mmol), and triethylamine (0.165 mL, 1.18 mmol) was dissolved in n-propanol (5.91 mL) and purged with nitrogen for 5 minutes in a sealed tube. The solution was heated at 100° C. for 18 h. the reaction was cooled to room temperature and quenched with saturated sodium bicarbonate. The aqueous layer was extracted with ethyl acetate (×3) and the organic layers combined, dried with magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by flash chromatography to afford the title compound as an orange solid. 1H NMR (500 MHz, CD3SOCD3) δ 8.61 (d, 1H); 8.23 (d, 1H); 8.16 (s, 1H); 7.95 (s, 1H); 7.32 (dd, 1H); 6.94 (dd, 1H); 5.87 (d, 1H); 5.44 (d, 1H); 3.85 (s, 3H). LRMS (APCI) calc'd for (C14H11N3O2S) [M+11]+, 286.1. found 286.0.

Workup

  1. custompurged with nitrogen for 5 minutes in a sealed tube
  2. temperaturewas cooled to room temperature
  3. customquenched with saturated sodium bicarbonate
  4. extractionThe aqueous layer was extracted with ethyl acetate (×3)
  5. dry with materialdried with magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-0380dd10f42642c48eda19af5f695715
Source dataset
uspto-grants-2013_11
Patent number
US08592425B2

Reaction notes

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