N,N,N',N'-Tetramethylethylenediamine → {1-[tert-Butyl(dimethyl)silyl]-5-fluoro-1H-indol-4-yl}boronic acid
Reaction equation
[Si:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([F:17])=[CH:14][CH:15]=2)[CH:10]=[CH:9]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].CN(CCN(C)C)C.[Li]C(CC)C.[B:31](OC(C)C)([O:36]C(C)C)[O:32]C(C)C>C1COCC1.C1CCCCC1.O>[Si:1]([N:8]1[C:16]2[C:11](=[C:12]([B:31]([OH:36])[OH:32])[C:13]([F:17])=[CH:14][CH:15]=2)[CH:10]=[CH:9]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]Participants
8
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- -78 °C
Procedure
To a mixture of the product of Step 1 (4.98 g, 20 mmol) and TMEDA (2.32 g, 20 mmol) in THF at −78° C. was slowly added a 1.3M solution of s-BuLi (15.4 mL, 20 mmol) in cyclohexane and the mixture was stirred for 2 h at −78° C. Triisopropyl borate (3.76 g, 20 mmol) was added to the mixture at −78° C. and stirred for another 1 h and then warmed to −20° C. Water was added and the mixture was extracted with EtOAc and the organic layer was dried over Na2SO4 and evaporated. The residue was re-crystallized (EtOAc and n-hexane) to give the title compound (1.2 g, 20.7%).
Workup
- stirringstirred for another 1 h
- temperaturewarmed to −20° C
- extractionthe mixture was extracted with EtOAc
- dry with materialthe organic layer was dried over Na2SO4
- customevaporated
- customThe residue was re-crystallized (EtOAc and n-hexane)
Sources & evidence
- ORD record
- ord-acbecb1c68394dcabecf931a52a1896f
- Source dataset
- uspto-grants-2015_09
- Patent number
- US09133180B2
Reaction notes
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