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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

HRID 1490506
Notes
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Reaction equation

HRID 1490506 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)cc21
ParticipantsConditionsProcedureSources & evidenceReaction notes

Participants

7

Reactant 1

HCID 117162536-fluoro-1-[tris(propan-2-yl)silyl]-1H-indole

Product 1

HCID 667609686-Fluoro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)-1-(triisopropylsilyl)-indoleYield 53%

Reagents, catalysts & solvents 5

HCID 6425PinacolReagentHCID 8471TriethylamineReagentHCID 67506CatecholboraneReagent

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
DOI
10.1002/anie.201611536

Reaction notes

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On this pageParticipantsConditionsProcedureSources & evidenceReaction notes
HCID 582056
Tris(pentafluorophenyl)borane
Catalyst
HCID 1140TolueneSolvent