Pyridine, 2-(trimethylsilyl)- → Methyl 1-{[4-(pyridin-2-yl)phenyl]sulfonyl}piperidine-4-carboxylate

HRID 1913163Notes

Reaction equation

I[C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[CH2:16][CH2:15][CH:14]([C:17]([O:19][CH3:20])=[O:18])[CH2:13][CH2:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.C[Si](C)(C)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>CN(C)C=O.[Ag-]=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[N:24]1[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=1[C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[CH2:16][CH2:15][CH:14]([C:17]([O:19][CH3:20])=[O:18])[CH2:13][CH2:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 90 °C

Procedure

To a stirred suspension of methyl 1-[(4-iodophenyl)sulfonyl]piperidine-4-carboxylate (1.97 g, 4.81 mmol) and 2-(trimethylsilyl)pyridine (2.0 mL), 14.5 mmol) in anhydrous N,N-dimethyl formamide (50 mL) is added silver (I) oxide (1.12 g, 4.82 mmol), tetrakis(triphenylphosphine)palladium (0.28 g, 5 mol %) and tetrabutyl ammonium fluoride (1M in THF, 0.48 mL). The reaction is heated at 90° C. for 18 h. The reaction mixture is filtered and washed with EtOAc. The filtrate is concentrated under reduced pressure. Purification by column chromatography (silica, eluent: heptane, 5-75% EtOAc) gives 0.87 g (50%) of methyl 1-{[4-(pyridin-2-yl)phenyl]sulfonyl}piperidine-4-carboxylate. m/z=361 [M++H].

Workup

filtrationThe reaction mixture is filtered
washwashed with EtOAc
concentrationThe filtrate is concentrated under reduced pressure
customPurification by column chromatography (silica, eluent: heptane, 5-75% EtOAc)

Sources & evidence

ORD record: ord-5d2c642126d34c0aaa4435ea72b96f65
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08609696B2

Reaction notes

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