6-Methoxy-1H-indole-3-carboxaldehyde → 1-cyclopropyl-6-methoxy-1H-indole-3-carbaldehyde

Dihydroxo-bis[N,N,N′,N′-tetramethylenediamine)copper (II) chloride (26 mg, 0.057 mmol) was added to a stirred room temperature mixture of 6-methoxy-1H-indole-3-carbaldehyde (100 mg, 0.568 mmol) and cyclopropylboronic acid (98 mg, 1.13 mmol) in dichloromethane (3 mL). Molecular sieves (4 A°, 100 mg) were added and the mixture was stirred under oxygen at room temperature for 48 hours. The reaction mixture was filtered over a pad of silica gel, washed with dichloromethane, partitioned between dichloromethane (10 mL) and 10% ammonium hydroxide (2×10 mL). The organic layer was washed with water (10 mL) and brine (10 mL). The organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography (Biotage 25 M), eluting with EtOAc/hexanes to give the title compound (50 mg) as a oil.

1. additionMolecular sieves (4 A°, 100 mg) were added
2. filtrationThe reaction mixture was filtered over a pad of silica gel
3. washwashed with dichloromethane
4. custompartitioned between dichloromethane (10 mL) and 10% ammonium hydroxide (2×10 mL)
5. washThe organic layer was washed with water (10 mL) and brine (10 mL)
6. dry with materialThe organic layer was dried over sodium sulfate
7. filtrationfiltered
8. concentrationconcentrated under reduced pressure
9. customThe residue was purified by flash chromatography (Biotage 25 M)
10. washeluting with EtOAc/hexanes

ORD record

ord-bd40677a9d6c4dbc9e8ae4271c401b3c

Source dataset

uspto-grants-2014_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08742110B2