Diisopropylethylamine → 2-{4-[(4-Chlorophenyl)sulfonyl]piperidin-1-yl}-4-(trifluoromethyl)pyridine

HRID 1868066Notes

Reaction equation

HRID 1868066 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.Cl[C:18]1[CH:23]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:21]=[CH:20][N:19]=1.CCN(C(C)C)C(C)C>O1CCOCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([CH:11]2[CH2:16][CH2:15][N:14]([C:18]3[CH:23]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:21]=[CH:20][N:19]=3)[CH2:13][CH2:12]2)(=[O:9])=[O:10])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 1449582-Chloro-4-(trifluoromethyl)pyridineHCID 27610724-[(4-Chlorophenyl)sulfonyl]piperidine

Product 1

HCID 685519242-{4-[(4-Chlorophenyl)sulfonyl]piperidin-1-yl}-4-(trifluoromethyl)pyridineYield 32%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Using the procedure from Example 1A, 4-[(4-chlorophenyl)sulfonyl]piperidine (100 mg, 0.38 mmol) was reacted with 2-chloro-4-(trifluoromethyl)pyridine (99 μl, 0.76 mmol), DIEA (0.27 ml, 1.52) and 1,4-dioxane (0.3 ml) at 190° C. to afford the title compound (49 mg), an off-white solid, in 32% yield.

Sources & evidence

ORD record
ord-c4e3d4a8cf6549b39e6e23a9cb60445a
Source dataset
uspto-grants-2009_12
Patent number
US07632838B2

Reaction notes

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