HCID 62491089, compound → HCID 178431092, compound

HRID 1490790Notes

Reaction equation

HRID 1490790 reaction equation
O=C(NCCc1ccccn1)C(F)(F)F>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.C[OH2+].C[OH2+].[Ir].[Ir]>CC1(C)OB(c2ccc(CCNC(=O)C(F)(F)F)nc2)OC1(C)C.CC1(C)OB(c2ccnc(CCNC(=O)C(F)(F)F)c2)OC1(C)C

Participants

7

Reactant 1

HCID 62491089HCID 62491089, compound

Product 2

HCID 178431049HCID 178431049, compoundYield 29%HCID 178431092HCID 178431092, compoundYield 58%

Reagents, catalysts & solvents 4

HCID 2733548Bis(pinacolato)diboraneReagentHCID 42491874,4'-Di-tert-butyl-2,2'-bipyridylReagentHCID 76001521Bis(1,5-cyclooctadiene)dimethoxydiiridiumCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
35 °C

Procedure

Following general procedure F using 4m (54.5 mg, 0.25 mmol), B2pin2 (95.2 mg, 0.375 mmol), [Ir(COD)OMe]2 (2.5 mg, 0.00375 mmol) and dtbpy (2.0 mg, 0.0075 mmol) in THF (1.25 mL). Stirred in vial at 35 °C for 6 hours. Analysis of crude 1 H NMR using internal standard 1,2‐dimethoxyethane showed 2:1:0.4 meta:para:di(3,5) borylation (overall meta:para borylation 1.4:1) in 99% yield. Purification by silica gel chromatography proved not to be possible, leading to product decomposition. As such, the compounds was characterised from the crude, which contained pinacol borane impurity. By subtracting the resonances for the meta isomer, the NMR data of the para and di(3,5) borylated isomer can be assigned as follows:

Sources & evidence

ORD record
ord-af69df40c0704093bfb3590bfae2a9e2
Source dataset
Borylation dataset from Roche

Reaction notes

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