3-Fluoro-N-trifluoroacetylbenzylamine → HCID 178431089, compound

HRID 1490752Notes

Reaction equation

HRID 1490752 reaction equation
O=C(NCc1cccc(F)c1)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]>CC1(C)OB(c2cc(F)cc(CNC(=O)C(F)(F)F)c2)OC1(C)C.CC1(C)OB(c2ccc(CNC(=O)C(F)(F)F)cc2F)OC1(C)C

Participants

7

Reactant 1

HCID 624921483-Fluoro-N-trifluoroacetylbenzylamine

Product 2

HCID 178431062HCID 178431062, compoundYield 21%HCID 178431089HCID 178431089, compoundYield 32%

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‐(3‐fluorobenzyl)acetamide (55.3 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 1.5:1 meta:para borylation in 53% yield. The crude product wassubjected to silica gel chromatography (Pet. Ether (40‐60):EtOAc (9:1) however significant decomposition was observed. A small para enriched fraction (1:2.7 meta:para isomerration by 1 H NMR)wasisolated as an off white solid (8 mg, 0.02 mmol, 9%). By subtracting the resonances for the meta isomer, the NMR data of the para isomer can be assigned as follows:

Sources & evidence

ORD record
ord-afeb48e6596546c1b243513811877044
Source dataset
Borylation dataset from Roche

Reaction notes

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