Trifluoroacetic acid → HCID 67466328, compound

HRID 2284368Notes

Reaction equation

HRID 2284368 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[C:8]1[C:9]2[N:10]([CH:14]=[CH:15][N:16]=2)[N:11]=[CH:12][CH:13]=1.[I:17]N1C(=O)CCC1=O.C(O)(C(F)(F)F)=O>C(Cl)(Cl)Cl>[I:17][C:14]1[N:10]2[N:11]=[CH:12][CH:13]=[C:8]([C:3]3[CH:4]=[N:5][CH:6]=[CH:7][C:2]=3[CH3:1])[C:9]2=[N:16][CH:15]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 120273N-IodosuccinimideHCID 67468662HCID 67468662, compound

Product 1

HCID 67466328HCID 67466328, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 8-(4-methylpyridin-3-yl)imidazo[1,2-b]pyridazine, (480 mg, 1.48 mmol) in CHCl3 (15 mL) were added N-iodo succinimide (400 mg, 1.776 mmol) and TFA (0.34 g, 2.96 mmol). The reaction mixture was stirred at room temperature for 2 h. The reaction mixture was quenched with saturated NaHCO3 and extracted with CH2Cl2. The combined organic layer was washed with water and brine, and dried over Na2SO4. The crude product was purified by BIOTAGE® (20-40% EtOAc/CH2Cl2; 1.2 L). 1H NMR (400 MHz, CDCl3) δ ppm 8.50-8.70 (3H, m), 7.90 (1H, s), 7.22-7.39 (4H, m), 7.06 (1H, d, J=4.53 Hz), 2.32 (3H, s); LC/MS: Rt=1.13 min. LC/MS (Condition A): 336.97.

Workup

  1. customThe reaction mixture was quenched with saturated NaHCO3
  2. extractionextracted with CH2Cl2
  3. washThe combined organic layer was washed with water and brine
  4. dry with materialdried over Na2SO4
  5. customThe crude product was purified by BIOTAGE® (20-40% EtOAc/CH2Cl2; 1.2 L)

Sources & evidence

ORD record
ord-1bac95b714bd43d2b513e8d55c73d501
Source dataset
uspto-grants-2015_09
Patent number
US09145419B2

Reaction notes

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