Isopropyl iodide → 4-Iodo-5-isopropoxy-2-methoxypyridine

HRID 56753Notes

Reaction equation

I[CH:2]([CH3:4])[CH3:3].C(=O)([O-])[O-].[K+].[K+].[I:11][C:12]1[CH:17]=[C:16]([O:18][CH3:19])[N:15]=[CH:14][C:13]=1[OH:20]>CC(C)=O>[I:11][C:12]1[C:13]([O:20][CH:2]([CH3:4])[CH3:3])=[CH:14][N:15]=[C:16]([O:18][CH3:19])[CH:17]=1

Participants

Conditions

Temperature: 80 °C

Procedure

At 0° C., 758 mg (4.5 mmol) of 2-iodopropane and 948 mg (6.9 mmol, 2 eq.) of potassium carbonate were added to a solution of 861 mg (3.4 mmol) of 4-iodo-6-methoxypyridin-3-ol in 15 ml of acetone and the mixture was stirred at 80° C. overnight and concentrated under reduced pressure. After addition of water/ethyl acetate and phase separation, the aqueous phase was extracted with ethyl acetate. The combined organic phases were dried (sodium sulphate), filtered and concentrated under reduced pressure. Yield: 741 mg (73% of theory)

Workup

concentrationconcentrated under reduced pressure
additionAfter addition of water/ethyl acetate and phase separation
extractionthe aqueous phase was extracted with ethyl acetate
dry with materialThe combined organic phases were dried (sodium sulphate)
filtrationfiltered
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-09a74957ad694955b0fe63b0e48009ab
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09434690B2

Reaction notes

Loading…