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

HRID 1490417Notes

Reaction equation

HRID 1490417 reaction equation
Cc1c[nH]c2ccccc12>C1=CCCC=CCC1.C1=CCCC=CCC1.C1CCOC1.CC(C)(C)c1ccnc(-c2cc(C(C)(C)C)ccn2)c1.CC1(C)OB(B2OC(C)(C)C(C)(C)O2)OC1(C)C.CC1(C)OBOC1(C)C.[Cl-].[Cl-].[Ir].[Ir]>Cc1c[nH]c2c(B3OC(C)(C)C(C)(C)O3)cccc12

Participants

7

Reactant 1

HCID 6736Skatole

Product 1

HCID 671738433-methyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indoleYield 61%

Reagents, catalysts & solvents 5

HCID 2733548Bis(pinacolato)diboraneReagentHCID 27347684,4,5,5-Tetramethyl[1,3,2]dioxaborolaneReagentHCID 42491874,4'-Di-tert-butyl-2,2'-bipyridylReagentHCID 82923Chloro-1,5-cyclooctadiene-iridium(I) dimerCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Sources & evidence

ORD record
ord-cb3768fd10fe448c90134711143bee97
Source dataset
Borylation dataset from Roche

Reaction notes

Loading…