Potassium Phosphate, Tribasic → 4-(2-Fluoropyridin-3-YL)cyclohex-3-enol
Reaction equation
[O-]P([O-])([O-])=O.[K+].[K+].[K+].FC(F)(F)S(O[C:15]1[CH2:20][CH2:19][CH:18]([O:21][Si](C(C)(C)C)(C)C)[CH2:17][CH:16]=1)(=O)=O.[F:31][C:32]1[C:37](B(O)O)=[CH:36][CH:35]=[CH:34][N:33]=1>>[F:31][C:32]1[C:37]([C:15]2[CH2:20][CH2:19][CH:18]([OH:21])[CH2:17][CH:16]=2)=[CH:36][CH:35]=[CH:34][N:33]=1Participants
Procedure
To a 25 mL microwave vial was added potassium phosphate tribasic (0.354 mL, 4.27 mmol), PdCl2(AmPhos) (0.121 g, 0.171 mmol), 4-(tert-butyldimethylsilyloxy)cyclohex-1-enyl trifluoromethanesulfonate (0.616 g, 1.710 mmol), and 2-fluoropyridin-3-ylboronic acid (0.265 g, 1.881 mmol) before evacuating and backfilling with nitrogen (3×). A mixed solvent of Dioxane (7.12 mL):water (1.425 mL) was added, and the contents were irradiated at 150° C. for 30 minutes in an Initiator microwave reactor (Personal Chemistry, Biotage AB, Inc., Upssala, Sweden). The biphasic solution was diluted with water and extracted with DCM (3×25 mL) before drying over sodium sulfate, filtering, and concentrating under reduced pressure to a dark brown residue. The residue was taken up in 5 mL DCM and applied directly to silica (0 to 70% ethyl acetate/hexanes for followed by 5 to 10% MeOH/DCM). The resulting yellow oil was taken forward without further manipulation.
Workup
- custombefore evacuating
- additionA mixed solvent of Dioxane (7.12 mL):water (1.425 mL) was added
- customthe contents were irradiated at 150° C. for 30 minutes in an Initiator microwave reactor (Personal Chemistry, Biotage AB, Inc., Upssala, Sweden)
- additionThe biphasic solution was diluted with water
- extractionextracted with DCM (3×25 mL)
- dry with materialbefore drying over sodium sulfate
- filtrationfiltering
- concentrationconcentrating under reduced pressure to a dark brown residue
Sources & evidence
- ORD record
- ord-2be0277c29d6440188db673d24a8ecd7
- Source dataset
- uspto-grants-2014_01
- Patent number
- US08637500B2
Reaction notes
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