2,2,2-trifluoro-N-(pyridin-2-ylmethyl)acetamide → HCID 178431093, compound

HRID 1490757Notes

Reaction equation

HRID 1490757 reaction equation
O=C(NCc1ccccn1)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]>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 8%HCID 178431093HCID 178431093, compoundYield 61%

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
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 1a (3.8 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 8.0:1:1 C4:C5‐borylation:SM in 69% yield. The crude product was unable to be purified by silica gel chromatography, however a small sample of the C4 product was isolated clean from flushing the silica with EtOAc (mixed fractions) followed by 20% MeOH in EtOAc (clean C4 fraction) as an off white solid (9.9 mg, 0.03 mmol, 12%):

Sources & evidence

ORD record
ord-49f1636090474cb3ba6ada2b6f7c62d6
Source dataset
Borylation dataset from Roche

Reaction notes

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