HCID 3869638, compound → HCID 178427430, compound

HRID 1490759Notes

Reaction equation

HRID 1490759 reaction equation
Cc1ccc(S(=O)(=O)NCc2ccccc2C(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(S(=O)(=O)NCc2cc(B3OC(C)(C)C(C)(C)O3)ccc2C(F)(F)F)cc1.Cc1ccc(S(=O)(=O)NCc2ccc(B3OC(C)(C)C(C)(C)O3)cc2C(F)(F)F)cc1

Participants

7

Reactant 1

HCID 3869638HCID 3869638, compound

Product 2

HCID 178427430HCID 178427430, compoundYield 63%HCID 178427431HCID 178427431, compoundYield 25%

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 4‐methyl‐N‐(2‐(trifluoromethyl)benzyl)benzenesulfonamide (82.3 mg, 0.25 mmol), B2pin2 (95 mg, 0.375 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 solventsremoved. Analysis of crude 1 H NMR using internalstandard 1,2‐dimethoxyethane showed 2.5:1 meta:para borylation in 88% yield. The crude product was purified by silica gel chromatography (Pet. Ether (40‐60):EtOAc (9:1) to give the title compound (as a 17:35:1 mixture of meta:para ratio as determined by 1 H NMR) as a white solid (93 mg), due to the presence of the SM the NMR yield was used for all comparisons. Using a combination of 2D NMR analysis the meta and para isomers are described:

Sources & evidence

ORD record
ord-173c24ef61a34f5987b98d11e9b04bdc
Source dataset
Borylation dataset from Roche

Reaction notes

Loading…