1-Methyl-2,3-dihydro-1H-indole → 1-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1H-indole

HRID 1490498Notes

Reaction equation

HRID 1490498 reaction equation
CN1CCc2ccccc21>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>CN1CCc2cc(B3OC(C)(C)C(C)(C)O3)ccc21

Participants

7

Reactant 1

HCID 558301-Methyl-2,3-dihydro-1H-indole

Product 1

HCID 242295911-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1H-indoleYield 32%

Reagents, catalysts & solvents 5

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

Conditions

Temperature
100 °C

Procedure

Prepared from 1-methylindoline (1j, 26.6 mg, 0.200 mmol, 1.00 equiv) and catBH (36.0 mg, 0.300 mmol, 1.50 equiv) at 100 o C according to GP 1. The title compound was purified by flash column chromatography using cyclohexane/EtOAc/Et3N (30/1/1) as eluent to afford 3j (16.6 mg, 32%) as a white solid.

Sources & evidence

ORD record
ord-5720a54c12234aecb4e32125f1ec4073
Source dataset
Borylation dataset from Roche

Reaction notes

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