Sodium hydride → HCID 59375120, compound

A solution of 3-bromo-2-methylaniline (2.00 g, 10.75 mmol) in DCM (20 mL) was treated with TEA (3.00 mL, 21.50 mmol) and then with a solution of 4-bromobutanoyl chloride (2.392 g, 12.90 mmol) in DCM (10 mL), and the resulting mixture was stirred at rt. After 2.5 h, the mixture was diluted with DCM, washed with NaHCO3 (aq) and water, and dried and concentrated. The residue was dissolved in THF (20 mL) and treated with hexane-washed sodium hydride (60% oil dispersion, 0.860 g, 21.50 mmol). The mixture was stirred at rt for 1.5 h, then was concentrated. The residue was dissolved in DCM, washed with water, 1 M hydrochloric acid and brine, and dried and concentrated. The residue was purified by column chromatography (eluting with a gradient from 80:20 hexane-EtOAc to EtOAc) to provide N-(3-bromo-2-methylphenyl)cyclopropanecarboxamide (900 mg, 33%) as a white solid. Mass spectrum m/z 254, 256 (M+H)+.

1. washwashed with NaHCO3 (aq) and water
2. customdried
3. concentrationconcentrated
4. dissolutionThe residue was dissolved in THF (20 mL)
5. additiontreated with hexane-
6. concentrationwas concentrated
7. dissolutionThe residue was dissolved in DCM
8. washwashed with water, 1 M hydrochloric acid and brine
9. customdried
10. concentrationconcentrated
11. customThe residue was purified by column chromatography (
12. washeluting with a gradient from 80:20 hexane-EtOAc to EtOAc)

ORD record

ord-7ca013800e854c90a7f2fbe18fa14f6b

Source dataset

uspto-grants-2011_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08084620B2