Anisole → (5R)-5-[(E)-2-(5-bromo-6-methoxypyridin-2-yl)-2-(4-tert-butylphenyl)ethenyl]pyrrolidin-2-one

HRID 70555Notes

Reaction equation

C1(OC)C=CC=CC=1.[Br:9][C:10]1[CH:11]=[CH:12][C:13](/[C:18](/[C:37]2[CH:42]=[CH:41][C:40]([C:43]([CH3:46])([CH3:45])[CH3:44])=[CH:39][CH:38]=2)=[CH:19]/[C@@H:20]2[N:24](CC3C=CC(OC)=CC=3OC)[C:23](=[O:36])[CH2:22][CH2:21]2)=[N:14][C:15]=1[O:16][CH3:17]>FC(F)(F)C(O)=O>[Br:9][C:10]1[CH:11]=[CH:12][C:13](/[C:18](/[C:37]2[CH:38]=[CH:39][C:40]([C:43]([CH3:46])([CH3:45])[CH3:44])=[CH:41][CH:42]=2)=[CH:19]/[C@@H:20]2[NH:24][C:23](=[O:36])[CH2:22][CH2:21]2)=[N:14][C:15]=1[O:16][CH3:17]

Participants

Conditions

Temperature: 70 °C

Procedure

Trifluoroacetic acid (10 mL) and anisole (5 mL) were added to (5R)-5-[(E)-2-(5-bromo-6-methoxypyridin-2-yl)-2-(4-tert-butylphenyl)ethenyl]-1-(2,4-dimethoxybenzyl)pyrrolidin-2-one (950 mg), and the mixture was stirred at 70° C. for five hours. The reaction solution was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1→1:4) to give the title compound as a yellow amorphous (460 mg, 66%).

Workup

concentrationThe reaction solution was concentrated under reduced pressure
customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1→1:4)

Sources & evidence

ORD record: ord-fd21d88dc4d14a0d8ab015c72803c5e2
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08822503B2

Reaction notes

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