HCID 178523285, compound → HCID 178431091, compound

HRID 1490809Notes

Reaction equation

HRID 1490809 reaction equation
O=C(NCCCc1ccccn1)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(CCCNC(=O)C(F)(F)F)nc2)OC1(C)C.CC1(C)OB(c2ccnc(CCCNC(=O)C(F)(F)F)c2)OC1(C)C

Participants

7

Reactant 1

HCID 178523285HCID 178523285, compound

Product 2

HCID 178431041HCID 178431041, compoundYield 8%HCID 178431091HCID 178431091, compoundYield 63%

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
25 °C

Procedure

Following general procedure F using 2,2,2‐trifluoro‐N‐(3‐(pyridin‐2‐yl)propyl)acetamide (58.1 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 rt for 15 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 71% yield. The crude product was unable to be purified by silica gel chromatography and was hence characterised from the crude mixture.

Sources & evidence

ORD record
ord-f79b8ef401de4d298e3e84f06ee0cf1a
Source dataset
Borylation dataset from Roche

Reaction notes

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