Acetic Acid → 4-[2-(5-Bromo-pyridin-2-ylamino)-ethyl]-tetrahydro-pyran-4-carboxylic acid methyl ester
Reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH2:8])=[N:6][CH:7]=1.ClC(Cl)C.[CH3:13][O:14][C:15]([C:17]1([CH2:23][CH:24]=O)[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1)=[O:16].C(O)(=O)C.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[CH3:13][O:14][C:15]([C:17]1([CH2:23][CH2:24][NH:8][C:5]2[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][N:6]=2)[CH2:18][CH2:19][O:20][CH2:21][CH2:22]1)=[O:16]Participants
7
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 5-bromopyridin-2-amine (0.488 g, 2.82 mmol) in 1-2 dichloroethane (DCE, 10 mL) was added desired 4-(2-oxo-ethyl)-tetrahydro-pyran-4-carboxylic acid methyl ester (0.529 g, 2.82), acetic acid (3.1 eq) and allowed to stir at room temperature for an hour. NaBH(OAc)3 (3 eq) was then added in one portion and reaction mixture allowed to stir at room temperature for 16 hours. The reaction mixture was then diluted with DCM (10 mL), quenched with 2 M of NH4OH in water. The aqueous layer was extracted with DCM (10 mL×2). The combined organic layers were washed with aqueous NaHCO3 (30 mL), brine (30 mL), and dried over Na2SO4, and concentrated under vacuum.
Workup
- stirringto stir at room temperature for 16 hours
- customquenched with 2 M of NH4OH in water
- extractionThe aqueous layer was extracted with DCM (10 mL×2)
- washThe combined organic layers were washed with aqueous NaHCO3 (30 mL), brine (30 mL)
- dry with materialdried over Na2SO4
- concentrationconcentrated under vacuum
Sources & evidence
- ORD record
- ord-1ce9037896ae4782af7e7b40aefd4a15
- Source dataset
- uspto-grants-2014_08
- Patent number
- US08796278B2
Reaction notes
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