2-Methylbenzylamine, TFA → HCID 178423575, compound

HRID 1490745Notes

Reaction equation

HRID 1490745 reaction equation
Cc1ccccc1CNC(=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]>Cc1cc(B2OC(C)(C)C(C)(C)O2)ccc1CNC(=O)C(F)(F)F.Cc1ccc(B2OC(C)(C)C(C)(C)O2)cc1CNC(=O)C(F)(F)F

Participants

7

Reactant 1

HCID 233835502-Methylbenzylamine, TFA

Product 2

HCID 178422408HCID 178422408, compoundYield 10%HCID 178423575HCID 178423575, compoundYield 80%

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‐(2‐methylbenzyl)acetamide (54.3 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 7.8:1 meta:para borylation in 93% yield. The crude product was purified by silica gel chromatography (Pet. Ether (40‐60):EtOAc (17:3)* to give the title compound (as a 7.7:1 mixture of meta:para ratio, as determined by 1 H NMR) as a white solid (77 mg, 0.20 mmol, 90%).

Sources & evidence

ORD record
ord-37675a7c1a59458aa3050aae7ba4465a
Source dataset
Borylation dataset from Roche

Reaction notes

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