Potassium Carbonate → HCID 86679135, compound
Reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[N:6][CH:7]=1.C([O-])([O-])=O.[K+].[K+].[C:15]([O:19][C:20]([N:22]1[CH2:25][CH:24](Br)[CH2:23]1)=[O:21])([CH3:18])([CH3:17])[CH3:16].C([O-])(O)=O.[Na+]>CN(C=O)C.CCOC(C)=O>[C:15]([O:19][C:20]([N:22]1[CH2:25][CH:24]([O:8][C:4]2[CH:5]=[N:6][CH:7]=[C:2]([Br:1])[CH:3]=2)[CH2:23]1)=[O:21])([CH3:18])([CH3:16])[CH3:17]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 60 °C
Procedure
To a solution of 5-bromopyridin-3-ol (0.285 g, 1.64 mmol) in DMF (2.5 mL) was added K2CO3 (0.453 g, 3.28 mmol), followed by 3-bromo-azetidine-1-carboxylic acid tert-butyl ester (0.425 g, 1.8 mmol) in DMF (0.5 mL) and the reaction mixture was heated to 60° C. and stirred over night. The reaction mixture was diluted with EtOAc, poured into sat. NaHCO3 solution (10 mL) and the aqueous layer was extracted EtOAc (2×20 mL). Combined organics were washed with brine, dried over Na2SO4, filtered and evaporated to dryness. The residue was purified by silica gel flash chromatography eluting with a 0 to 50% EtOAc-heptane gradient to give the title compound (0.539 g, 100%) as a colorless crystalline solid. MS: 329.1 (M+H+).
Workup
- extractionthe aqueous layer was extracted EtOAc (2×20 mL)
- washCombined organics were washed with brine
- dry with materialdried over Na2SO4
- filtrationfiltered
- customevaporated to dryness
- customThe residue was purified by silica gel flash chromatography
- washeluting with a 0 to 50% EtOAc-heptane gradient
Sources & evidence
- ORD record
- ord-f46151f629f04261814d12a71ad0993b
- Source dataset
- uspto-grants-2016_02
- Patent number
- US09260408B2
Reaction notes
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