Methyl 2-[[(2,2,2-trifluoroacetyl)amino]methyl]benzoate → HCID 178497424, compound

HRID 1490755Notes

Reaction equation

HRID 1490755 reaction equation
COC(=O)c1ccccc1CNC(=O)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]>COC(=O)c1cc(B2OC(C)(C)C(C)(C)O2)ccc1CNC(=O)C(F)(F)F.COC(=O)c1ccc(B2OC(C)(C)C(C)(C)O2)cc1CNC(=O)C(F)(F)F

Participants

7

Reactant 1

HCID 59461373Methyl 2-[[(2,2,2-trifluoroacetyl)amino]methyl]benzoate

Product 2

HCID 178497025HCID 178497025, compoundYield 10%HCID 178497424HCID 178497424, compoundYield 78%

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 methyl 2‐((2,2,2‐trifluoroacetamido)methyl)benzoate using (65.3 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 7.3:1 meta:para borylation in 89% yield. The crude product was purified by silica gel chromatography (Pet. Ether (40‐60):EtOAc (9:1) to give the title compound (as a 7.4:1 mixture of meta:para ratio, as determined by 1 H NMR) as a white solid (85.3 mg, 0.22 mmol, 88%).

Sources & evidence

ORD record
ord-c5b07dacb4474bfe89f614c6fcb70f56
Source dataset
Borylation dataset from Roche

Reaction notes

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