HCID 14511476, compound → HCID 178431010, compound

HRID 1490811Notes

Reaction equation

HRID 1490811 reaction equation
O=C(NC1CCc2ccccc21)C(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]>CC1(C)OB(c2ccc3c(c2)CCC3NC(=O)C(F)(F)F)OC1(C)C.CC1(C)OB(c2cccc3c2CCC3NC(=O)C(F)(F)F)OC1(C)C

Participants

7

Reactant 1

HCID 14511476HCID 14511476, compound

Product 2

HCID 178431010HCID 178431010, compoundYield 30%HCID 178431029HCID 178431029, compoundYield 20%

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‐(2,3‐dihydro‐1H‐inden‐1‐yl)‐2,2,2‐trifluoroacetamide (11a) (57.3 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 11:18:20:30* dimeta:meta1:meta2:para borylation in 79% yield. The crude product was purified by silica gel chromatography (Pet. Ether (40‐60):EtOAc (19:1‐9:1) to give the title compound in 2 fractions: as pale brown oil containing the meta 2 product and SM in a 3:1 ratio, and as a colourless oil containing the dimeta, meta 1 and para products in a 1:2:2.8 ratio. NMR yields have been used for clarity.

Sources & evidence

ORD record
ord-0cc3e0c817c7449595b6677a83c8fc24
Source dataset
Borylation dataset from Roche

Reaction notes

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