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1-(Triisopropylsilyl)indole → HCID 11395451, compound

HRID 1490502
Notes
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Reaction equation

HRID 1490502 reaction equation
CC(C)[Si](C(C)C)(C(C)C)n1ccc2ccccc21>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)c2ccccc21
ParticipantsConditionsProcedureSources & evidenceReaction notes

Participants

7

Reactant 1

HCID 114599991-(Triisopropylsilyl)indole

Product 1

HCID 11395451HCID 11395451, compoundYield 63%

Reagents, catalysts & solvents 5

HCID 6425PinacolReagentHCID 8471TriethylamineReagentHCID 67506CatecholboraneReagentHCID 582056Tris(pentafluorophenyl)boraneCatalyst

Conditions

Temperature
120 °C

Procedure

Prepared from N-(triisopropylsilyl)-1H-indole (4a, 54.7 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 6a (50.3 mg, 63%) as a slightly yellow oil.

Sources & evidence

ORD record
ord-60618b7fc5b54d599ac4309f26d5cb76
Source dataset
Borylation dataset from Roche
DOI
10.1002/anie.201611536

Reaction notes

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On this pageParticipantsConditionsProcedureSources & evidenceReaction notes
HCID 1140TolueneSolvent