Pyrazole → HCID 66759809, compound

HRID 1850418Notes

Reaction equation

[H-].[Na+].[NH:3]1[CH:7]=[CH:6][CH:5]=[N:4]1.[Br:8][C:9]1[C:10]([CH3:23])=[C:11]([CH3:22])[C:12]2[O:16][C:15]([CH2:18]I)([CH3:17])[CH2:14][C:13]=2[C:20]=1[CH3:21].[Cl-].[NH4+]>C(OCC)(=O)C.CN(C=O)C>[Br:8][C:9]1[C:10]([CH3:23])=[C:11]([CH3:22])[C:12]2[O:16][C:15]([CH2:17][N:3]3[CH:7]=[CH:6][CH:5]=[N:4]3)([CH3:18])[CH2:14][C:13]=2[C:20]=1[CH3:21]

Participants

Conditions

Temperature: 0 °C

Procedure

60% sodium hydride (91 mg, 2.27 mmol) was added to a solution of DMF (2 mL) containing pyrazole (155 mg, 2.27 mmol) under ice-cooling condition, and the mixture was stirred at 0° C. for 20 minutes. After that, a solution of DMF (1.5 mL) containing 5-bromo-2-(iodomethyl)-2,4,6,7-tetramethyl-2,3-dihydro-1-benzofuran (300 mg, 0.759 mmol) synthesized in Reference Example 133 was added thereto, and the mixture was stirred at 100° C. for 4 hours and at 120° C. for 2 hours. After cooled to room temperature, the reaction solution was distributed using a saturated ammonium chloride aqueous solution and ethyl acetate. The organic layer was washed with saturated saline, and dried using anhydrous magnesium sulfate, followed by concentration under reduced pressure. The residue was purified by silica gel chromatography (hexane-ethyl acetate 95:5-85:15) to give 185 mg of the title compound (yield: 71%).

Workup

temperaturecooling condition
customsynthesized in Reference Example 133
additionwas added
stirringthe mixture was stirred at 100° C. for 4 hours and at 120° C. for 2 hours
temperatureAfter cooled to room temperature
washThe organic layer was washed with saturated saline
customdried
concentrationfollowed by concentration under reduced pressure
customThe residue was purified by silica gel chromatography (hexane-ethyl acetate 95:5-85:15)

Sources & evidence

ORD record: ord-90a49e4568fd49f49e7339a23bf541ea
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08957069B2

Reaction notes

Loading…