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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
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인쇄 미리보기

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HRID 1490567 반응식
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
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참가 물질

6

반응물 1

HCID 35329801-(Tert-butoxycarbonyl)indole

생성물 1

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

시약·촉매·용매 4

HCID 2733548Bis(pinacolato)diborane시약HCID 1223807993-pyridin-2-yl-2-(3-pyridin-2-yl-1H-1,3,2-benzodiazaborol-2-yl)-1H-1,3,2-benzodiazaborole시약HCID 76001521Bis(1,5-cyclooctadiene)dimethoxydiiridium

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온도
75 °C

실험 절차

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.

출처 및 근거

ORD 기록
ord-79db2c6eef514d27b2130b1758eb40ff
출처 데이터셋
Borylation dataset from Roche
DOI
10.1021/jacs.5b05252

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촉매
HCID 138539Cyclopentyl methyl ether용매