Trifluoroacetic acid → HCID 67464524, compound

HRID 2284374Notes

Reaction equation

HRID 2284374 reaction equation
[N:1]1[CH:2]=[CH:3][N:4]2[C:9]=1[C:8]([C:10]1[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]=[N:12][CH:11]=1)=[CH:7][CH:6]=[N:5]2.[I:20]N1C(=O)CCC1=O.C(O)(C(F)(F)F)=O>C(Cl)(Cl)Cl>[I:20][C:3]1[N:4]2[N:5]=[CH:6][CH:7]=[C:8]([C:10]3[C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[CH:13]=[N:12][CH:11]=3)[C:9]2=[N:1][CH:2]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 120273N-IodosuccinimideHCID 67466955HCID 67466955, compound

Product 1

HCID 67464524HCID 67464524, compoundYield 87.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a solution of 4-(imidazo[1,2-b]pyridazin-8-yl)isoquinoline (220 mg, 0.893 mmol) in CHCl3 (10 mL) were added N-iodo succinimide (241 mg, 1.072 mmol) and TFA (0.275 mL, 3.57 mmol) In CHCl3 (1 mL). The reaction mixture was stirred at room temperature for 2 h and quenched with saturated NaHCO3. The layers were separated and the combined organic layer was washed with water and brine, dried over Na2SO4. The crude product was purified by BIOTAGE® (30-70% EtOAc/CH2Cl2, 0.8 L) to give the product (290 mg, 87%). 1H NMR (400 MHz, CDCl3) δ ppm 9.41 (1H, s), 8.72 (1H, s), 8.66 (1H, d, J=4.53 Hz), 8.07-8.17 (1H, m), 7.90 (1H, s), 7.71 (3H, d, J=3.02 Hz), 7.28 (3H, s), 7.26 (1H, d, J=4.53 Hz); LC/MS: Rt=1.53 min. LC/MS (Condition A): 373.08.

Workup

  1. customquenched with saturated NaHCO3
  2. customThe layers were separated
  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® (30-70% EtOAc/CH2Cl2, 0.8 L)

Sources & evidence

ORD record
ord-392ebc8c7f694b49a1c6babe3fe85c7c
Source dataset
uspto-grants-2015_09
Patent number
US09145419B2

Reaction notes

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