Dimethylformamide → 8-[3-Fluoro-5-(trifluoromethyl)pyridin-2-yl]-1,4-dioxa-8-azaspiro[4.5]decane
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.Br[C:12]1[C:17]([F:18])=[CH:16][C:15]([C:19]([F:22])([F:21])[F:20])=[CH:14][N:13]=1.CN(C)C=O.O1CCOCC1>C(N(CC)CC)C>[F:18][C:17]1[C:12]([N:8]2[CH2:9][CH2:10][C:5]3([O:4][CH2:3][CH2:2][O:1]3)[CH2:6][CH2:7]2)=[N:13][CH:14]=[C:15]([C:19]([F:21])([F:20])[F:22])[CH:16]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 120 °C
Procedure
A mixture of 1,4-dioxa-8-azaspiro[4.5]decane (1.76 g), 2-bromo-3-fluoro-5-(trifluoromethyl)-pyridine (2.95 g), N,N-dimethylformamide (50 mL), 1,4-dioxane (75 mL) and triethylamine (5.07 ml) is stirred in a sealed vessel at 120° C. for 1 h. After cooling to room temperature, the mixture is concentrated and partitioned between ethyl acetate (100 mL) and water (100 mL). The water layer is extracted with ethyl acetate (100 mL) and the combined organic layers are dried over Na2SO4, filtered and concentrated to yield the title compound.
Workup
- temperatureAfter cooling to room temperature
- concentrationthe mixture is concentrated
- custompartitioned between ethyl acetate (100 mL) and water (100 mL)
- extractionThe water layer is extracted with ethyl acetate (100 mL)
- dry with materialthe combined organic layers are dried over Na2SO4
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-6801e119df3b400d8406cd16cd51ab70
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08822471B2
Reaction notes
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