5-PHENYLDIPYRROMETHANE → HCID 264043, compound

Exemplified for 1-(4-Methylbenzoyl)-5-phenyldipyrromethane (2a). A solution of EtMgBr (50.0 mL, 50.0 mmol, 1.0 M in THF) was added via syringe to a stirred solution of 1a (4.44 g, 20.0 mmol) in THF (20 mL) under argon. The mixture was stirred for 10 min at room temperature and then cooled to −78° C. A solution of 6a (4.58 g, 20.0 mmol) in THF (20 mL) was added. The mixture was stirred for 10 min at −78° C. Then the cooling bath was removed, the mixture was stirred for 20 min, and then the reaction was quenched with saturated aqueous NH4Cl (150 mL). The mixture was diluted with THF (10 mL), washed with water (100 mL), and then dried (Na2SO4). Removal of solvents and chromatography [silica (6×24 cm), CH2Cl2 (2300 mL)] afforded a golden amorphous solid (5.82 g, 86%): mp 69-70° C.; 1H NMR δ 2.43 (s, 3H), 5.55 (s, 1H), 5.95-6.01 (m, 1H), 6.05-6.09 (m, 1H), 6.14-6.18 (m, 1H), 6.67-6.71 (m, 1H), 6.79-6.82 (m, 1H), 7.20-7.35 (m, 7H), 7.72-7.76 (m, 2H), 8.05-8.22 (brs, 1H), 9.50-9.68 (brs, 1H); Anal. Calcd for C23H20N2O: C, 81.15; H, 5.92; N, 8.23. Found: C, 80.74; H, 5.74; N, 8.25.

1. temperaturecooled to −78° C
2. stirringThe mixture was stirred for 10 min at −78° C
3. customThen the cooling bath was removed
4. stirringthe mixture was stirred for 20 min
5. customthe reaction was quenched with saturated aqueous NH4Cl (150 mL)
6. additionThe mixture was diluted with THF (10 mL)
7. washwashed with water (100 mL)
8. dry with materialdried (Na2SO4)
9. customRemoval of solvents and chromatography [silica (6×24 cm), CH2Cl2 (2300 mL)]

ORD record

ord-3a9a1dc13ece4f87a4d0e343b041226c

Source dataset

uspto-grants-2005_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06924375B2