HCID 178423712, compound → HCID 178423698, compound

HRID 1490807Notes

Reaction equation

HRID 1490807 reaction equation
Cc1ccc(-c2ccccc2CCCNC(=O)C(F)(F)F)cc1>C1=CCCC=CCC1.C1=CCCC=CCC1.C1CCOC1.CC1(C)OB(B2OC(C)(C)C(C)(C)O2)OC1(C)C.CCCC[N+](CCCC)(CCCC)CCCC.C[OH2+].C[OH2+].Cc1ccc(-c2ccc(CS(=O)(=O)[O-])cn2)nc1.[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 9%HCID 178423698HCID 178423698, compoundYield 83%

Reagents, catalysts & solvents 4

HCID 2733548Bis(pinacolato)diboraneReagentHCID 165587889Tetrabutylazanium {5'-methyl-[2,2'-bipyridin]-5-yl}methanesulfonateReagentHCID 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 1a (3.8 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 10.4:1 meta:para borylation in 99% 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 9.5:1 mixture of meta:para ratio, as determined by 1 H NMR) as a white solid (102.4 mg, 0.23 mmol, 92%).

Sources & evidence

ORD record
ord-7a7ce259d48648448218c44b7d39ce2e
Source dataset
Borylation dataset from Roche

Reaction notes

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