Potassium Iodide → HCID 66674804, compound

HRID 422571Notes

Reaction equation

HRID 422571 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5](N)=[CH:4][C:3]=1[C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[C:15]([O:19][C@H:20]([CH3:25])[C:21]([F:24])([F:23])[F:22])=[N:14][N:13]=[CH:12]2.N([O-])=O.[Na+].[I-:30].[K+]>Cl.O>[I:30][C:5]1[CH:6]=[CH:7][C:2]([CH3:1])=[C:3]([C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[C:15]([O:19][C@H:20]([CH3:25])[C:21]([F:23])([F:24])[F:22])=[N:14][N:13]=[CH:12]3)[CH:4]=1

Participants

6

Reactant 3

HCID 4875Potassium IodideHCID 23668193Sodium NitriteHCID 66675979HCID 66675979, compound

Product 1

HCID 66674804HCID 66674804, compoundYield 73.1%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent2×

Procedure

To a suspension of 4-methyl-3-(1-((R)-1,1,1-trifluoropropan-2-yloxy)phthalazin-6-yl)benzenamine (1.49 g, 4.30 mmol) in 14 mL of 6N HCl at 0° C. was added sodium nitrite (593 mg, 8.59 mmol) in 8 mL of water drop wise. After 20 min at 0° C., a solution of potassium iodide (2.14 g, 12.89 mmol) in 6 mL of water was added slowly. After the brown heterogeneous mixture was stirred at RT for 1 h, it was extracted twice with DCM. The combined DCM layers were washed with 1 N NaOH followed by sat. sodium thiosulfate, dried and concentrated. The brown residue was purified on an ISCO 40 g column (25-55% EtAc in Hexanes) to provide 6-(5-iodo-2-methylphenyl)-1-((R)-1,1,1-trifluoropropan-2-yloxy)phthalazine (73% yield, 1.44 g) as an off-white amorphous solid. MS (ESI, pos. ion) m/z: 459.0 (M+1).

Workup

  1. extractionit was extracted twice with DCM
  2. washThe combined DCM layers were washed with 1 N NaOH
  3. customdried
  4. concentrationconcentrated
  5. customThe brown residue was purified on an ISCO 40 g column (25-55% EtAc in Hexanes)

Sources & evidence

ORD record
ord-0961ab672cc84b13a016a283b69409ba
Source dataset
uspto-grants-2012_01
Patent number
US08101612B2

Reaction notes

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