Potassium Iodide → 2-(2-tert-Butylphenoxy)-3-iodopyridine

HRID 555420Notes

Reaction equation

N([O-])=O.[Na+].[C:5]([C:9]1[CH:22]=[CH:21][CH:20]=[CH:19][C:10]=1[O:11][C:12]1[C:17](N)=[CH:16][CH:15]=[CH:14][N:13]=1)([CH3:8])([CH3:7])[CH3:6].[I-:23].[K+].S(=O)(O)[O-].[Na+]>O.Cl>[C:5]([C:9]1[CH:22]=[CH:21][CH:20]=[CH:19][C:10]=1[O:11][C:12]1[C:17]([I:23])=[CH:16][CH:15]=[CH:14][N:13]=1)([CH3:8])([CH3:7])[CH3:6]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of sodium nitrite (157 mg, 2.28 mmol) in water (1 mL) was added to a mixture of 2-(2-tert-butylphenoxy)-3-aminopyridine (prepared above according to 1b) (500 mg, 2.07 mmol) in (1:1) conc. HCl:water (14 mL) at 0° C. The mixture was stirred at 0° C. for 15 min and a solution of potassium iodide (1.0 g, 6.22 mmol) in water (2 mL) was added. The mixture was stirred at 60° C. for 1.5 h and allowed to cool down to rt. A solution of sodium bisulfite was added and the mixture was extracted with ethyl acetate (3×50 mL). The combined organic layers were dried (anhydrous sodium sulfate), filtered and evaporated. The residue was purified by flash-chromatography (dichloromethane:hexanes/20:100) to afford 394 mg (56%) of 2-(2-tert-butylphenoxy)-3-iodopyridine. (M+H)+=354.

Workup

customat 0° C
stirringThe mixture was stirred at 60° C. for 1.5 h
temperatureto cool down to rt
extractionthe mixture was extracted with ethyl acetate (3×50 mL)
dry with materialThe combined organic layers were dried (anhydrous sodium sulfate)
filtrationfiltered
customevaporated
customThe residue was purified by flash-chromatography (dichloromethane:hexanes/20:100)

Sources & evidence

ORD record: ord-78efb93cf5ef48d08ac290d86d370b86
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08053450B2

Reaction notes

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