Tetrahydrofuran → 3-Methyl-5-(5-(trifluoromethyl)pyridin-2-yloxy)phenylboronic acid
Reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:16]=[C:17]([CH3:19])[CH:18]=1)[O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]([F:15])([F:14])[F:13])=[CH:8][N:7]=1.C([O:23][B:24](OC(C)C)[O:25]C(C)C)(C)C.C1COCC1.[Li]CCCC>C1(C)C=CC=CC=1>[CH3:19][C:17]1[CH:18]=[C:2]([B:24]([OH:25])[OH:23])[CH:3]=[C:4]([O:5][C:6]2[CH:11]=[CH:10][C:9]([C:12]([F:15])([F:14])[F:13])=[CH:8][N:7]=2)[CH:16]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -40 °C
Procedure
2-(3-Bromo-5-methylphenoxy)-5-(trifluoromethyl)pyridine (2 g, 0.006 mol) and triisopropylborate (1.66 mL, 0.0072 mol) were dissolved in toluene (40 mL) and THF (20 mL) and cooled to −78° C. n-BuLi (5.38 mL, 0.006 mol) was added while maintaining the reaction at −70° C. The reaction was stirred for 1 h at −40° C. Gradually the temperature was increased to −20-0° C. and the reaction was quenched with 2NHCl. The reaction mixture was warmed to RT, concentrated and extracted with EtOAc. The organic extract was dried over Na2SO4 and concentrated under reduced pressure to give the title compound (2.16 g).
Workup
- additionwas added
- temperaturewhile maintaining
- customthe reaction at −70° C
- temperatureGradually the temperature was increased to −20-0° C.
- customthe reaction was quenched with 2NHCl
- temperatureThe reaction mixture was warmed to RT
- concentrationconcentrated
- extractionextracted with EtOAc
- extractionThe organic extract
- dry with materialwas dried over Na2SO4
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-1bdae19e4c0d42208b2cb67c11935435
- Source dataset
- uspto-grants-2011_10
- Patent number
- US08044052B2
Reaction notes
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