Dichloromethane → (5-Amino-6-methoxypyridin-3-yl)boronic acid
Reaction equation
Br[C:2]1[CH:3]=[C:4]([NH2:10])[C:5]([O:8][CH3:9])=[N:6][CH:7]=1.[B:11]1(B2OC(C)(C)C(C)(C)O2)[O:15]C(C)(C)C(C)(C)[O:12]1.C([O-])(=O)C.[K+].C(Cl)Cl>O1CCOCC1.C(OCC)(=O)C>[NH2:10][C:4]1[CH:3]=[C:2]([B:11]([OH:15])[OH:12])[CH:7]=[N:6][C:5]=1[O:8][CH3:9]Participants
7
Procedure
5-bromo-2-methoxypyridin-3-amine (2 g, 9.85 mmol, commercially available), Bis(pinacolato)diboron (11.82 mmol), potassium acetate (1.4 g) and (1,1-bis(diphenylphosphino)ferrocene)-dichloropalladium (II) complex with DCM (200 mg, commercially available) was dissolved in dioxane (75 mL) under argon atmosphere. The reaction mixture was refluxed for 8 h. The reaction mixture was cooled, diluted with ethyl acetate (75 mL) and filtered. The filtrate was concentrated. The crude product was purified over silica gel using 0-10% ethyl acetate in petroleum ether to obtain the titled boronic acid derivative.
Workup
- temperatureThe reaction mixture was refluxed for 8 h
- temperatureThe reaction mixture was cooled
- filtrationfiltered
- concentrationThe filtrate was concentrated
- customThe crude product was purified over silica gel using 0-10% ethyl acetate in petroleum ether
Sources & evidence
- ORD record
- ord-7373ca9bee894c108a1bcdabe8fc6123
- Source dataset
- uspto-grants-2015_06
- Patent number
- US09062046B2
Reaction notes
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