Triisopropyl borate → [1-(Tert-butoxycarbonyl)-1H-pyrrolo[2,3-B]pyridin-2-YL]boronic acid
Reaction equation
[N:1]1([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[CH:2]1.[B:17](OC(C)C)([O:22]C(C)C)[O:18]C(C)C.[Li+].CC([N-]C(C)C)C>C1COCC1>[C:13]([O:12][C:10]([N:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[C:2]1[B:17]([OH:22])[OH:18])=[O:11])([CH3:16])([CH3:15])[CH3:14]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of tert-butyl 1H-pyrrolo[2,3-b]pyridine-1-carboxylate (2.18 g, 10 mmol) and B(OiPr)3 (2.8 mL, 12.1 mmol) in 10 mL of THF cooled at 0° C. was added a LDA solution (16 mmol, prepared from 2.24 mL of iPr2NH, 15 mL of THF and 6.4 mL of 2.5 M n-BuLi solution in hexane) by a syringe pump over a period of 2 h. The reaction mixture was stirred for additional 1 h at 0° C. before being quenched by addition of 30 mL of pH 7 sodium phosphate buffer solution. The product was extracted with 2×100 mL of EtOAc. The extracts were dried over Na2SO4, filtered, and concentrated under vacuum to give 3 g of the title compounds as a gray solid which was used for the next step without further purification.
Workup
- custombefore being quenched by addition of 30 mL of pH 7 sodium phosphate buffer solution
- extractionThe product was extracted with 2×100 mL of EtOAc
- dry with materialThe extracts were dried over Na2SO4
- filtrationfiltered
- concentrationconcentrated under vacuum
Sources & evidence
- ORD record
- ord-5edf8c0fa1864de1b409075932004585
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08946445B2
Reaction notes
Loading…