HCID 24754945, compound → HCID 54671452, compound

HRID 1490505Notes

Reaction equation

HRID 1490505 reaction equation
CC(C)[Si](C(C)C)(C(C)C)n1ccc2cc(Cl)ccc21>B1Oc2ccccc2O1.CC(C)(O)C(C)(C)O.CCN(CC)CC.Clc1ccccc1.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)c2cc(Cl)ccc21

Participants

7

Reactant 1

HCID 24754945HCID 24754945, compound

Product 1

HCID 54671452HCID 54671452, compoundYield 59%

Reagents, catalysts & solvents 5

HCID 6425PinacolReagentHCID 8471TriethylamineReagentHCID 67506CatecholboraneReagentHCID 582056Tris(pentafluorophenyl)boraneCatalystHCID 7964ChlorobenzeneSolvent

Conditions

Temperature
120 °C

Procedure

Prepared from 5-chloro-N-(triisopropylsilyl)-1H-indole (4e, 30.7 mg, 0.100 mmol, 1.00 equiv) and catBH (48.0 mg, 0.400 mmol, 4.00 equiv) in chlorobenzene according to GP 2. The title compound was purified by flash column chromatography using cyclohexane/EtOAc/Et3N (30/1/1) as eluent to afford 6e[S4] (25.5 mg, 59%) as a white foam.

Sources & evidence

ORD record
ord-53e329e21ef444c4ac0a77bc66bd8fcd
Source dataset
Borylation dataset from Roche

Reaction notes

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