2-Methoxybenzylamine, N-trifluoroacetyl- → HCID 178486938, compound

HRID 1490748Notes

Reaction equation

HRID 1490748 reaction equation
COc1ccccc1CNC(=O)C(F)(F)F>C1=CCCC=CCC1.C1=CCCC=CCC1.C1CCOC1.CC(C)(C)c1ccnc(-c2cc(C(C)(C)C)ccn2)c1.CC1(C)OB(B2OC(C)(C)C(C)(C)O2)OC1(C)C.C[OH2+].C[OH2+].[Ir].[Ir]>COc1cc(B2OC(C)(C)C(C)(C)O2)ccc1CNC(=O)C(F)(F)F.COc1ccc(B2OC(C)(C)C(C)(C)O2)cc1CNC(=O)C(F)(F)F

Participants

7

Reactant 1

HCID 624912582-Methoxybenzylamine, N-trifluoroacetyl-

Product 2

HCID 178486938HCID 178486938, compoundYield 39%HCID 178488281HCID 178488281, compoundYield 20%

Reagents, catalysts & solvents 4

HCID 2733548Bis(pinacolato)diboraneReagentHCID 42491874,4'-Di-tert-butyl-2,2'-bipyridylReagentHCID 76001521Bis(1,5-cyclooctadiene)dimethoxydiiridiumCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

Following general procedure F using 2,2,2‐Trifluoro‐N‐(2‐methoxybenzyl)acetamide (58.3 mg, 0.25 mmol), B2pin2 (127 mg, 0.50 mmol), [Ir(COD)OMe]2 (2.5 mg, 0.00375 mmol) and dtbpy (2.0 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 1:2 meta:para borylation in 70% yield. The crude product was purified by silica gel chromatography (Pet. Ether (40‐60):EtOAc (19:1) to give the title compound (as a 1:2 mixture of meta:para ratio, as determined by 1 H NMR) as a colourless oil (53.1 mg, 0.15 mmol, 59%).

Sources & evidence

ORD record
ord-77a974ad7b754ffb94b6a3f6496ee1e6
Source dataset
Borylation dataset from Roche

Reaction notes

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