Hydrogen Peroxide → HCID 24826839, compound
Reaction equation
Br[C:2]1[C:3]([O:15][C:16]2[C:21]([F:22])=[CH:20][CH:19]=[CH:18][C:17]=2[F:23])=[CH:4][C:5]([NH:8][C:9]2[S:10][CH:11]=[C:12]([CH3:14])[N:13]=2)=[N:6][CH:7]=1.[Li]C.C([Li])CCC.C([O:34]B(OC(C)C)OC(C)C)(C)C.[OH-].[Na+].OO>C1COCC1.CO>[F:23][C:17]1[CH:18]=[CH:19][CH:20]=[C:21]([F:22])[C:16]=1[O:15][C:3]1[CH:4]=[C:5]([NH:8][C:9]2[S:10][CH:11]=[C:12]([CH3:14])[N:13]=2)[N:6]=[CH:7][C:2]=1[OH:34]Participants
Reactant 6
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- -78 °C
Procedure
N-(5-bromo-4-(2,6-difluorophenoxy)pyridin-2-yl)-4-methylthiazol-2-amine (2.66 mmol) is dissolved in THF (30 mL) and cooled to −78° C. MeLi (2.07 mL, 3.32 mmol) is slowly added and the reaction mixture is stirred for 10 minutes. n-Butyllithium (1.33 mL, 3.32 mmol) is added and the reaction mixture is stirred for 15 minutes. Triisopropylborate (0.613 mL, 2.66 mmol) is added and the reaction mixture is stirred for 30 minutes. The reaction mixture is warmed to 0° C., and methanol (5 mL), 10% aqueous NaOH (5.1 mL, 12.8 mmol), and 30% aqueous H2O2 (1.27 mL, 13.3 mmol) are added. The reaction mixture is stirred at 0° C. for 1 hour, then purified by silica gel chromatography (10-20% EtOAc in hexanes) to afford 4-(2,6-difluorophenoxy)-6-(4-methylthiazol-2-ylamino)pyridin-3-ol.
Workup
- stirringthe reaction mixture is stirred for 15 minutes
- stirringthe reaction mixture is stirred for 30 minutes
- temperatureThe reaction mixture is warmed to 0° C.
- stirringThe reaction mixture is stirred at 0° C. for 1 hour
- custompurified by silica gel chromatography (10-20% EtOAc in hexanes)
Sources & evidence
- ORD record
- ord-b9c42f97119041dfab2f38e8fd3824f4
- Source dataset
- uspto-grants-2011_09
- Patent number
- US08022222B2
Reaction notes
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