Diisopropylethylamine → 4-{4-[(4-Tert-butylphenyl)sulfonyl]piperidin-1-yl}-3,5-dichloropyridine

HRID 1868068Notes

Reaction equation

HRID 1868068 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([CH:14]2[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]2)(=[O:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[Cl:20][C:21]1[CH:22]=[N:23][CH:24]=[C:25]([Cl:28])[C:26]=1Cl.CCN(C(C)C)C(C)C>O1CCOCC1>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([S:11]([CH:14]2[CH2:15][CH2:16][N:17]([C:26]3[C:25]([Cl:28])=[CH:24][N:23]=[CH:22][C:21]=3[Cl:20])[CH2:18][CH2:19]2)(=[O:13])=[O:12])=[CH:9][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 37865313,4,5-TrichloropyridineHCID 185386364-[(4-Tert-butylphenyl)sulfonyl]piperidine

Product 1

HCID 685509124-{4-[(4-Tert-butylphenyl)sulfonyl]piperidin-1-yl}-3,5-dichloropyridineYield 10.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Using the procedure from Example 7A, 4-[(4-tert-butylphenyl)sulfonyl]piperidine (100 mg, 0.36 mmol) was reacted with 3,4,5-trichloropyridine (134 mg, 0.72 mmol), DIEA (0.25 ml, 1.44) and 1,4-dioxane (0.3 ml) at 185° C. to afford the title compound (16 mg), a white solid, in 10% yield.

Sources & evidence

ORD record
ord-fecc9e56feea42f38df962bcfe439a9d
Source dataset
uspto-grants-2009_12
Patent number
US07632838B2

Reaction notes

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