HCID 178453188, compound → HCID 178453130, compound

HRID 1490772Notes

Reaction equation

HRID 1490772 reaction equation
CC(C)(C)OC(=O)NCCc1ccccc1C(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]>CC(C)(C)OC(=O)NCCc1cc(B2OC(C)(C)C(C)(C)O2)ccc1C(F)(F)F.CC(C)(C)OC(=O)NCCc1ccc(B2OC(C)(C)C(C)(C)O2)cc1C(F)(F)F

Participants

7

Reactant 1

HCID 178453188HCID 178453188, compound

Product 2

HCID 178453130HCID 178453130, compoundYield 51%HCID 178453140HCID 178453140, compoundYield 39%

Reagents, catalysts & solvents 4

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

Conditions

Temperature
50 °C

Procedure

Following general procedure F using 4c (72.3 mg, 0.25 mmol), B2pin2 (127 mg, 0.50 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 50 °C for 20 hours. Analysis of crude 1 H NMR using internal standard 1,2‐dimethoxyethane showed 1.4:1 meta:para borylation in 99% yield. The crude product was purified by silica gel chromatography (10% EtOAc in Petroleum Ether 40‐60 o C) gave the title compound (as a 1.3:1 mixture of meta:para ratio, as determined by 1 H NMR) as a white solid (94 mg, 0.23 mmol, 90%). By subtracting the resonances for the meta isomer, the NMR data of the para isomer can be assigned as follows:

Sources & evidence

ORD record
ord-d1717d388ebf412d9553633ff7f10f3f
Source dataset
Borylation dataset from Roche

Reaction notes

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