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

HRID 1490567
Notes
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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
ParticipantsConditionsProcedureSources & evidenceReaction notes

Participants

6

Reactant 1

HCID 35329801-(Tert-butoxycarbonyl)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-benzodiazaboroleReagent

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
DOI
10.1021/jacs.5b05252

Reaction notes

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On this pageParticipantsConditionsProcedureSources & evidenceReaction notes
HCID 76001521
Bis(1,5-cyclooctadiene)dimethoxydiiridium
Catalyst
HCID 138539Cyclopentyl methyl etherSolvent