2,2,2-trifluoro-N-(pyridin-2-ylmethyl)acetamide → HCID 178431065, compound

HRID 1490758Notes

Reaction equation

HRID 1490758 reaction equation
O=C(NCc1ccccn1)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(c2ccc(CNC(=O)C(F)(F)F)nc2)OC1(C)C.CC1(C)OB(c2ccnc(CNC(=O)C(F)(F)F)c2)OC1(C)C

Participants

7

Reactant 1

HCID 41590022,2,2-trifluoro-N-(pyridin-2-ylmethyl)acetamide

Product 2

HCID 178431065HCID 178431065, compoundYield 24%HCID 178431093HCID 178431093, compoundYield 24%

Reagents, catalysts & solvents 4

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

Conditions

Temperature
35 °C

Procedure

Following general procedure F using 2,2,2‐trifluoro‐N‐(pyridin‐2‐ylmethyl)acetamide (51.0 mg, 0.25 mmol), B2pin2 (95 mg, 0.375 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 35 °C for 20 hours before cooling and the solvents removed. Analysis of crude 1 H NMR using internal standard 1,2‐dimethoxyethane showed 30:30:16:9 C4:C5:C3,5‐borylation:SM in 60% yield. The crude product was unable to be purified by silica gel chromatography and was hence characterised from the crude. By subtracting the resonances for the C4 isomer, SM, and using a combination of 2D NMR analysis the NMR data of the C5 and C3,5 isomers can be assigned as follows:

Sources & evidence

ORD record
ord-0bd9c183abf54fad9114a6cef7cfc4a3
Source dataset
Borylation dataset from Roche

Reaction notes

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