HCID 178423712, compound → HCID 178423658, compound

HRID 1490808Notes

Reaction equation

HRID 1490808 reaction equation
Cc1ccc(-c2ccccc2CCCNC(=O)C(F)(F)F)cc1>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]>Cc1ccc(-c2cc(B3OC(C)(C)C(C)(C)O3)ccc2CCCNC(=O)C(F)(F)F)cc1.Cc1ccc(-c2ccc(B3OC(C)(C)C(C)(C)O3)cc2CCCNC(=O)C(F)(F)F)cc1

Participants

7

Reactant 1

HCID 178423712HCID 178423712, compound

Product 2

HCID 178423658HCID 178423658, compoundYield 45%HCID 178423698HCID 178423698, compoundYield 40%

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 2,2,2‐trifluoro‐N‐(3‐(4'‐methyl‐[1,1'‐biphenyl]‐2‐ yl)propyl)acetamide (80.3 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). The reaction was stirred at 50 °C for 20 hours before cooling and the solvents removed. Analysis of crude 1 H NMR using internal standard 1,2‐dimethoxyethane showed 1:1 meta:para borylation in 100% yield. The crude product was purified by silica gel chromatography (Pet. Ether (40‐60):EtOAc (19:1‐9:1) to give the title compound (as a 1:1.1 mixture of meta:para ratio, as determined by 1 H NMR) as a colourless oil (95.0 mg, 0.21 mmol, 85%). 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-eb6a4f0ef1c8412f97d547e3d41c490b
Source dataset
Borylation dataset from Roche

Reaction notes

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