Triethylamine → 5-{2-Benzyloxy-4-[(E)-2-(6-methoxypyridin-2-yl)-vinyl]-phenyl}-1,1-dioxo-2-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-3-one

HRID 660482Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([CH:15]=[CH2:16])[CH:12]=[CH:11][C:10]=1[N:17]1[S:21](=[O:23])(=[O:22])[N:20]([CH2:24][CH2:25][Si:26]([CH3:29])([CH3:28])[CH3:27])[C:19](=[O:30])[CH2:18]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[C:32]1[CH:37]=[CH:36][CH:35]=[C:34]([O:38][CH3:39])[N:33]=1.CCN(CC)CC.C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C>C(#N)C.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH2:1]([O:8][C:9]1[CH:14]=[C:13](/[CH:15]=[CH:16]/[C:32]2[CH:37]=[CH:36][CH:35]=[C:34]([O:38][CH3:39])[N:33]=2)[CH:12]=[CH:11][C:10]=1[N:17]1[S:21](=[O:22])(=[O:23])[N:20]([CH2:24][CH2:25][Si:26]([CH3:28])([CH3:27])[CH3:29])[C:19](=[O:30])[CH2:18]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 5-(2-benzyloxy-4-vinylphenyl)-1,1-dioxo-2-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-3-one (Example 81, step A) (75 mg, 0.17 mmol) in acetonitrile (2 mL), in a pressure vessel, is added 2-bromo-6-methoxypyridine (32 mg, 0.17 mmol), NEt3 (0.05 mL, 0.34 mmol), Pd(OAc)2 (8 mg, 0.034 mmol), and 2-(di-t-butylphosphino)biphenyl (20 mg, 0.068 mmol). The vessel is sealed and stirred at 100° C. for 18 h. The reaction is cooled to RT and filtered through Celite. The solvent is removed under reduced pressure and the crude material purified by column chromatography using a gradient of 0-35% EtOAc/hexanes as eluent to afford the title compound as a yellow oil: (M+H)+=552.

Workup

customThe vessel is sealed
temperatureThe reaction is cooled to RT
filtrationfiltered through Celite
customThe solvent is removed under reduced pressure
customthe crude material purified by column chromatography

Sources & evidence

ORD record: ord-8a913bcb6e374713a02395ab6af2b54c
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08084448B2

Reaction notes

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