Sodium Carbonate → 5-bromo-N-[(1S)-1-cyclopropylethyl]pyridine-2-carboxamide
Reaction equation
[CH:1]1([C@@H:4]([NH2:6])[CH3:5])[CH2:3][CH2:2]1.[Br:7][C:8]1[CH:9]=[CH:10][C:11]([C:14](O)=[O:15])=[N:12][CH:13]=1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C.C([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl>[Br:7][C:8]1[CH:9]=[CH:10][C:11]([C:14]([NH:6][C@H:4]([CH:1]2[CH2:3][CH2:2]2)[CH3:5])=[O:15])=[N:12][CH:13]=1Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Procedure
(1S)-1-Cyclopropylethanamine (0.50 mL, 5.4 mmol, Alfa Aesar: Cat. #H27499) was added to a mixture of 5-bromopyridine-2-carboxylic acid (1.0 g, 5.0 mmol, Alfa Aesar: Cat. #B25675) in methylene chloride (30.0 mL), followed by benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (2.4 g, 5.4 mmol) and N,N-diisopropylethylamine (1.7 mL, 9.9 mmol). The reaction mixture was stirred at room temperature overnight. The reaction mixture was worked up with aqueous Na2CO3, and extracted with dichloromethylene (3×20 mL). The combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography on a silica gel column with ethyl acetate in hexanes (0-15%) to afford the desired product. LCMS (M+H)+: m/z=269.0/271.0.
Workup
- extractionextracted with dichloromethylene (3×20 mL)
- washThe combined organic layers were washed with brine
- dry with materialdried over MgSO4
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- customThe residue was purified by flash chromatography on a silica gel column with ethyl acetate in hexanes (0-15%)
Sources & evidence
- ORD record
- ord-fa80a1abf6714476a0a9b66d06fce9d1
- Source dataset
- uspto-grants-2015_05
- Patent number
- US09023840B2
Reaction notes
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