Dimethyl Sulfoxide → HCID 22047043, compound

Temperature

-78 °C

Oxalyl chloride (1.77 mL, 20.1 mmol) is combined with CH2Cl2 (60 mL) in a dried flask under nitrogen, cooled to −78° C., treated dropwise with DMSO (2.86 mL, 40.25 mmol) and stirred for 20 min. The cooled solution is treated drop-wise with a solution of (3-bromofuro[2,3-c]pyridin-5-yl)methanol (4.0 mg, 17.5 mmol) in THF (50 mL), stirred for 1 h, then treated drop-wise with Et3N (12.2 mL, 87.5 mmol). The mixture is stirred for 30 min at −78° C., then 30 min at 0° C. The mixture is washed with saturated NaHCO3 (120 mL) and the organics dried over K2CO3 and concentrated in vacuo to a dark yellow solid (3.91 g). The crude material is chromatographed over 150 g slurry-packed silica gel, eluting with 30% EtOAc/hexane. The appropriate fractions are combined and concentrated in vacuo to afford 3.93 g (99%) of 3-bromofuro[2,3-c]pyridine-5-carbaldehyde as a white solid. MS (EI) m/z: 225 (M+).

1. stirringstirred for 1 h
2. stirringThe mixture is stirred for 30 min at −78° C.
3. custom30 min
4. customat 0° C
5. washThe mixture is washed with saturated NaHCO3 (120 mL)
6. dry with materialthe organics dried over K2CO3
7. concentrationconcentrated in vacuo to a dark yellow solid (3.91 g)
8. customThe crude material is chromatographed over 150 g slurry-packed silica gel
9. washeluting with 30% EtOAc/hexane
10. concentrationconcentrated in vacuo

ORD record

ord-9c1f3543e4fe48409cb1416fec9ddc31

Source dataset

uspto-grants-2005_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06911543B2