Triisopropyl borate → HCID 67465561, compound
Reaction equation
C([Li])CCC.[C:6]([O:10][C:11]([N:13]1[CH2:18][CH:17]([CH3:19])[O:16][C:15]2[CH:20]=[C:21](Br)[CH:22]=[N:23][C:14]1=2)=[O:12])([CH3:9])([CH3:8])[CH3:7].C([O:28][B:29](OC(C)C)[O:30]C(C)C)(C)C>C1COCC1>[C:6]([O:10][C:11]([N:13]1[CH2:18][CH:17]([CH3:19])[O:16][C:15]2[CH:20]=[C:21]([B:29]([OH:30])[OH:28])[CH:22]=[N:23][C:14]1=2)=[O:12])([CH3:9])([CH3:8])[CH3:7]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
Butyl lithium (2.5 M in THF, 6.08 mL, 2.5 equiv.) was added dropwise into a stirring solution of 7-bromo-2-methyl-2,3-dihydro-pyrido[3,2-b][1,4]oxazine-4-carboxylic acid tert-butyl ester (2.0 g, 6.08 mmol, 1.0 equiv.) and triisopropylborate (2.86 g, 15.19 mmol, 2.5 equiv.) in anhydrous THF (20 mL) at −78° C. under nitrogen. The reaction was stirred at −78° C. and monitored with LCMS. After 2 hr, LCMS indicated the reaction complete. The reaction was quenched with water (20 mL) and concentrated under reduced pressure. The residue was washed with ether (2×10 mL) and the aqueous layer was placed in an ice-water bath. While stirring, 10 N HCl aqueous solution was carefully added dropwise until pH˜7. Filtration and washing with ice-water (3×5 mils) gave the desired product as a white solid (923 mg).
Workup
- customThe reaction was quenched with water (20 mL)
- concentrationconcentrated under reduced pressure
- washThe residue was washed with ether (2×10 mL)
- customthe aqueous layer was placed in an ice-water bath
- stirringWhile stirring
- addition10 N HCl aqueous solution was carefully added dropwise until pH˜7
- filtrationFiltration
- washwashing with ice-water (3×5 mils)
Sources & evidence
- ORD record
- ord-018983b990de4b88a8d242ae77c6f267
- Source dataset
- uspto-grants-2014_12
- Patent number
- US08916593B2
Reaction notes
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