2-Methylindole → 2-Methyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole

HRID 1490566Notes

Reaction equation

HRID 1490566 reaction equation
Cc1cc2ccccc2[nH]1>C1=CCCC=CCC1.C1=CCCC=CCC1.CC1(C)OB(B2OC(C)(C)C(C)(C)O2)OC1(C)C.COC1CCCC1.C[OH2+].C[OH2+].[Ir].[Ir].c1ccc(N2B(B3Nc4ccccc4N3c3ccccn3)Nc3ccccc32)nc1>Cc1cc2cccc(B3OC(C)(C)C(C)(C)O3)c2[nH]1

Participants

6

Reactant 1

HCID 72242-Methylindole

Product 1

HCID 249605942-Methyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indoleYield 64%

Reagents, catalysts & solvents 4

HCID 2733548Bis(pinacolato)diboraneReagentHCID 1223807993-pyridin-2-yl-2-(3-pyridin-2-yl-1H-1,3,2-benzodiazaborol-2-yl)-1H-1,3,2-benzodiazaboroleReagentHCID 76001521Bis(1,5-cyclooctadiene)dimethoxydiiridiumCatalystHCID 138539Cyclopentyl methyl etherSolvent

Conditions

Temperature
50 °C

Procedure

The general procedure A was followed using 2-methyl-1H-indole (65.6 mg, 0.5 mmol.) and B2pin2 (126.9 mg, 0.5 mmol, 1.0 eq.) as starting material. The resulting mixture was allowed to stir 16 hours at 50 oC. 5y was obtained as white solid (82.3 mg, 64 %) after purification by silica gel flash chromatography (EtOAc/PE=1:40 v/v). m.p.: 73-75 oC.

Sources & evidence

ORD record
ord-8a9da9cdfb524f499e336b80310520a5
Source dataset
Borylation dataset from Roche

Reaction notes

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