Diisopropylethylamine → 2-{4-[(4-Tert-butylphenyl)sulfonyl]piperidin-1-yl}-3-fluoropyridine

HRID 1868071Notes

Reaction equation

HRID 1868071 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[C:21]1[C:26]([F:27])=[CH:25][CH:24]=[CH:23][N:22]=1.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:21]3[C:26]([F:27])=[CH:25][CH:24]=[CH:23][N:22]=3)[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 27827912-Chloro-3-fluoropyridineHCID 185386364-[(4-Tert-butylphenyl)sulfonyl]piperidine

Product 1

HCID 685524082-{4-[(4-Tert-butylphenyl)sulfonyl]piperidin-1-yl}-3-fluoropyridineYield 10%

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 2-chloro-3-fluoropyridine (74 μl, 0.72 mmol), DIEA (0.25 ml, 1.44) and 1,4-dioxane (0.3 ml) at 185° C. to afford the title compound (13 mg), a white solid, in 10% yield.

Sources & evidence

ORD record
ord-6e19425bc0c5430ab443fb96ae62a68e
Source dataset
uspto-grants-2009_12
Patent number
US07632838B2

Reaction notes

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