HCID 24754943, compound → HCID 56924968, compound

HRID 1490504Notes

Reaction equation

HRID 1490504 reaction equation
Cc1ccc2c(ccn2[Si](C(C)C)(C(C)C)C(C)C)c1>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>Cc1ccc2c(c1)c(B1OC(C)(C)C(C)(C)O1)cn2[Si](C(C)C)(C(C)C)C(C)C

Participants

7

Reactant 1

HCID 24754943HCID 24754943, compound

Product 1

HCID 56924968HCID 56924968, compoundYield 75%

Reagents, catalysts & solvents 5

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

Conditions

Temperature
120 °C

Procedure

Prepared from 5-methyl-N-(triisopropylsilyl)-1H-indole (4d, 57.5 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 6d[S4] (62.0 mg, 75%) as a white foam.

Sources & evidence

ORD record
ord-147ffd4a44b54602a4cf9c7f7939ea78
Source dataset
Borylation dataset from Roche

Reaction notes

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