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

HRID 1490580Notes

Reaction equation

HRID 1490580 reaction equation
CCOC(=O)c1cc2cc(OC)ccc2[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]>CCOC(=O)c1cc2cc(OC)cc(B3OC(C)(C)C(C)(C)O3)c2[nH]1

Participants

6

Reactant 1

HCID 20926Ethyl 5-methoxyindole-2-carboxylate

Product 1

HCID 24960598Ethyl 5-methoxy-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-2-carboxylateYield 82%

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-acfe026613964bcfaefa7c284a88b1cd
Source dataset
Borylation dataset from Roche

Reaction notes

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