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

HRID 1490581Notes

Reaction equation

HRID 1490581 reaction equation
COC(=O)c1cc2c(OC)cccc2[nH]1>C1=CCCC=CCC1.C1=CCCC=CCC1.CC(C)(C)c1ccnc(-c2cc(C(C)(C)C)ccn2)c1.CC1(C)OBOC1(C)C.CCCCCC.C[OH2+].C[OH2+].[Ir].[Ir]>COC(=O)c1cc2c(OC)ccc(B3OC(C)(C)C(C)(C)O3)c2[nH]1

Participants

6

Reactant 1

HCID 688172methyl 4-methoxy-1H-indole-2-carboxylate

Product 1

HCID 53436934Methyl 4-methoxy-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-2-carboxylateYield 79%

Reagents, catalysts & solvents 4

HCID 27347684,4,5,5-Tetramethyl[1,3,2]dioxaborolaneReagentHCID 42491874,4'-Di-tert-butyl-2,2'-bipyridylReagentHCID 76001521Bis(1,5-cyclooctadiene)dimethoxydiiridiumCatalystHCID 8058HexaneSolvent

Conditions

Temperature
60 °C

Sources & evidence

ORD record
ord-9fccf3a399154e63a7c61b5aee5146a1
Source dataset
Borylation dataset from Roche

Reaction notes

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