1-Boc-indole → tert-Butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-1-carboxylate

HRID 1490567Notes

Reaction equation

HRID 1490567 reaction equation
CC(C)(C)OC(=O)n1ccc2ccccc21>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>CC(C)(C)OC(=O)n1cc(B2OC(C)(C)C(C)(C)O2)c2ccccc21

Participants

6

Reactant 1

HCID 35329801-Boc-indole

Product 1

HCID 49758860tert-Butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-1-carboxylateYield 65%

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
75 °C

Procedure

The general procedure A was followed using tert-butyl 1H-indole-1-carboxylate (108.7 mg, 0.5 mmol.) and B2(pin)2 (101.6 mg, 0.4 mmol, 0.8 eq.) as starting material. The resulting mixture was allowed to stir 16 hours at 75 oC. 5z was obtained as white solid (111.5 mg, 65 %) after purification by silica gel flash chromatography (EtOAc/PE=1:30 v/v). m.p.: 163-165 oC.

Sources & evidence

ORD record
ord-79db2c6eef514d27b2130b1758eb40ff
Source dataset
Borylation dataset from Roche

Reaction notes

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