Dimethylformamide → 1-(4-{2-[(3S)-3-{[tert-butyl(dimethyl)silyl]oxy}-1-pyrrolidinyl]ethoxy]phenyl}-4-[(5-chloro-2-pyridinyl)methoxy]-1H-pyridin-2-one

HRID 15075Notes

Reaction equation

Br[CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]3[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][N:20]=3)=[CH:13][C:12]2=[O:26])=[CH:7][CH:6]=1.[Si:27]([O:34][C@H:35]1[CH2:39][CH2:38][NH:37][CH2:36]1)([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:29])[CH3:28].C(N(C(C)C)C(C)C)C.CN(C=O)C>O>[Si:27]([O:34][C@H:35]1[CH2:39][CH2:38][N:37]([CH2:2][CH2:3][O:4][C:5]2[CH:10]=[CH:9][C:8]([N:11]3[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]4[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][N:20]=4)=[CH:13][C:12]3=[O:26])=[CH:7][CH:6]=2)[CH2:36]1)([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:29])[CH3:28]

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 1-[4(2-bromoethoxy)phenyl]-4-[(5-chloro-2-pyridinyl)methoxy]-1H-pyridin-2-one (300.7 mg, 0.69 mmol), (3S)-3-{[tert-butyl(dimethyl)silyl]oxy}pyrrolidine (417 mg, 2.1 mmols), ethyl (diisopropyl)amine (0.132 mL, 0.76 mmol) and DMF (3.5 mL) was stirred at 60° C. for 14 hours. Adding water, the reaction liquid was filtered. Thus obtained crude title compound was purified on silica gel column chromatography (KP-Sil FLASH 25+M, chloroform:methanol=1:0→10:1) to provide the title compound (276.6 mg, 72%).

Workup

filtrationwas filtered
customThus obtained crude title compound
customwas purified on silica gel column chromatography (KP-Sil FLASH 25+M, chloroform:methanol=1:0→10:1)

Sources & evidence

ORD record: ord-c1651b44d65c497cb22f6440b4333419
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07732456B2

Reaction notes

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