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

HRID 1490578Notes

Reaction equation

HRID 1490578 reaction equation
CCOC(=O)c1cc2cc(Cl)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(Cl)cc(B3OC(C)(C)C(C)(C)O3)c2[nH]1

Participants

6

Reactant 1

HCID 78518Ethyl 5-chloroindole-2-carboxylate

Product 1

HCID 24960597Ethyl 5-chloro-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-2-carboxylateYield 83%

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-970318500f0d417f974b01cd94c26ded
Source dataset
Borylation dataset from Roche

Reaction notes

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