6-fluoro-1-[tris(propan-2-yl)silyl]-1H-indole → 6-Fluoro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)-1-(triisopropylsilyl)-indole
Reaction equation
CC(C)[Si](C(C)C)(C(C)C)n1ccc2ccc(F)cc21>B1Oc2ccccc2O1.CC(C)(O)C(C)(C)O.CCN(CC)CC.Cc1ccccc1.Fc1c(F)c(F)c(B(c2c(F)c(F)c(F)c(F)c2F)c2c(F)c(F)c(F)c(F)c2F)c(F)c1F>CC(C)[Si](C(C)C)(C(C)C)n1cc(B2OC(C)(C)C(C)(C)O2)c2ccc(F)cc21Participants
7
Reactant 1
Product 1
Reagents, catalysts & solvents 5
Conditions
- Temperature
- 120 °C
Procedure
Prepared from 5-fluoro-N-(triisopropylsilyl)-1H-indole (4f, 58.3 mg, 0.200 mmol, 1.00 equiv) and catBH (96.0 mg, 0.800 mmol, 4.00 equiv) according to GP 2. The title compound was purified by flash column chromatography using cyclohexane/EtOAc/Et3N (30/1/1) as eluent to afford 6f (44.5 mg, 53%) as a white foam.
Sources & evidence
- ORD record
- ord-f00dc6f9b7b94e81a1e8412cdf01b4af
- Source dataset
- Borylation dataset from Roche
Reaction notes
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