m-Chloroperbenzoic acid → HCID 118497007, compound

3-chloroperbenzoic acid (80%, 4.83 g, 13.96 mmol) was added portion-wise to a solution of 5-chloro-2-(methoxymethyl)pyridine (Preparation 57, 2 g, 12.69 mmol) in DCM (50 mL) at 0° C. The reaction was stirred for 18 hours at room temperature. The reaction mixture was quenched with 2M aqueous sodium hydroxide (25 mL) and brine (25 mL) and stirred vigorously. The organic layer was collected, washed with 2M aqueous sodium hydroxide (2×10 mL), water (10 mL), dried over sodium sulfate and concentrated in vacuo. A portion of the residue (100 mg, 0.576 mmol) was stirred in phosphoryl chloride (2 mL) at 80° C. for 2 hours. The reaction was concentrated in vacuo and vigorously stirred in DCM (10 mL) and saturated aqueous sodium bicarbonate solution (10 mL) for 5 hours. The organic layer was collected dried over sodium sulphate and concentrated in vacuo. The residue was purified using silica gel column chromatography eluting with DCM to afford the title compound (38 mg, 34%).

1. customThe reaction mixture was quenched with 2M aqueous sodium hydroxide (25 mL) and brine (25 mL)
2. stirringstirred vigorously
3. customThe organic layer was collected
4. washwashed with 2M aqueous sodium hydroxide (2×10 mL), water (10 mL)
5. dry with materialdried over sodium sulfate
6. concentrationconcentrated in vacuo
7. concentrationThe reaction was concentrated in vacuo
8. stirringvigorously stirred in DCM (10 mL)
9. waitsaturated aqueous sodium bicarbonate solution (10 mL) for 5 hours
10. customThe organic layer was collected
11. dry with materialdried over sodium sulphate
12. concentrationconcentrated in vacuo
13. customThe residue was purified
14. washeluting with DCM

ORD record

ord-1c0fd9ab0003433782a6d245fb692e52

Source dataset

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09328096B2