1-(Triisopropylsilyl)indole → HCID 11395451, compound

HRID 1490503Notes

Reaction equation

HRID 1490503 reaction equation
CC(C)[Si](C(C)C)(C(C)C)n1ccc2ccccc21>B1Oc2ccccc2O1.C1=CC2C=CC1C2.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

Participants

8

Reactant 1

HCID 114599991-(Triisopropylsilyl)indole

Product 1

HCID 11395451HCID 11395451, compoundYield 61%

Reagents, catalysts & solvents 6

HCID 6425PinacolReagentHCID 8471TriethylamineReagentHCID 8473NorbornadieneReagentHCID 67506CatecholboraneReagentHCID 582056Tris(pentafluorophenyl)boraneCatalystHCID 1140TolueneSolvent

Conditions

Temperature
25 °C

Procedure

Prepared from N-(triisopropylsilyl)-1H-indole (4a, 27.4 mg, 0.100 mmol, 1.00 equiv), catBH (24.0 mg, 0.200 mmol, 2.00 equiv), norbornene (18.8 mg, 0.100 mmol, 1.00 equiv) and B(C6F5)3 (5.1 mg, 0.010 mmol, 0.10 equiv) according to GP 3. The title compound was purified by flash column chromatography using cyclohexane/EtOAc/Et3N (30/1/1) as eluent to afford 3j (24.4 mg, 61%) as a white solid.

Sources & evidence

ORD record
ord-15f394501a194234ab9754975d2d9bdd
Source dataset
Borylation dataset from Roche

Reaction notes

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