1,4-Dioxa-8-azaspiro(4.5)decane → 8-(2-Chloropyridin-4-yl)-1,4-dioxa-8-azaspiro[4.5]decane

HRID 451538Notes

Reaction equation

[O:1]1[C:5]2([CH2:10][CH2:9][NH:8][CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.[Cl:11][C:12]1[CH:17]=[C:16](F)[CH:15]=[CH:14][N:13]=1.C(N(CC)C(C)C)(C)C>O1CCOCC1>[Cl:11][C:12]1[CH:17]=[C:16]([N:8]2[CH2:9][CH2:10][C:5]3([O:4][CH2:3][CH2:2][O:1]3)[CH2:6][CH2:7]2)[CH:15]=[CH:14][N:13]=1

Participants

Conditions

Temperature: 120 °C

Procedure

To a solution of 1,4-dioxa-8-azaspiro[4.5]decane (895 μL, 6.98 mmol) and 2-chloro-4-fluoropyridine (1.01 g, 7.68 mmol) in dioxane (15 mL) was added N,N-diisopropylethylamine (1.83 mL, 10.5 mmol). Argon was bubbled through the reaction mixture for 5 minutes before it was heated to 120° C. in microwave for 3 hours. After evaporation, purification by chromatography (silica gel, 20 g, 30 to 10% ethyl acetate in heptane) afforded the title compound (1.3 g, 73%) as a yellow solid.

Workup

customArgon was bubbled through the reaction mixture for 5 minutes before it
customAfter evaporation, purification by chromatography (silica gel, 20 g, 30 to 10% ethyl acetate in heptane)

Sources & evidence

ORD record: ord-c728a78343ed48e0a8b9a3881c98642d
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08486967B2

Reaction notes

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