HCID 4271591, compound → HCID 178447270, compound

HRID 1490765Notes

Reaction equation

HRID 1490765 reaction equation
CC(C)(C)C(=O)NCc1ccccc1C(F)(F)F>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]>CC(C)(C)C(=O)NCc1cc(B2OC(C)(C)C(C)(C)O2)ccc1C(F)(F)F.CC(C)(C)C(=O)NCc1ccc(B2OC(C)(C)C(C)(C)O2)cc1C(F)(F)F

Participants

7

Reactant 1

HCID 4271591HCID 4271591, compound

Product 2

HCID 178447270HCID 178447270, compoundYield 72%HCID 178447271HCID 178447271, compoundYield 19%

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 N‐(2‐(trifluoromethyl)benzyl)pivalamide (64.8 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 wasstirred 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 3.8:1 meta:para borylation in 91% yield. The crude product was purified by silica gel chromatography (Pet. Ether (40‐ 60):EtOAc (19:1‐6:4) to give the title compound (as a 3.0:1 mixture of meta:para ratio as determined by 1 H NMR) as a white solid (69.1 mg, 0.18 mmol, 72%). Using a combination of 2D NMR analysis the meta and para isomers are described:

Sources & evidence

ORD record
ord-03493c8fbc6d4f73b834a599f010615a
Source dataset
Borylation dataset from Roche

Reaction notes

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