HCID 178497625, compound → HCID 178497422, compound

HRID 1490799Notes

Reaction equation

HRID 1490799 reaction equation
COC(=O)c1ccccc1CCCNC(=O)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]>COC(=O)c1cc(B2OC(C)(C)C(C)(C)O2)ccc1CCCNC(=O)C(F)(F)F.COC(=O)c1ccc(B2OC(C)(C)C(C)(C)O2)cc1CCCNC(=O)C(F)(F)F

Participants

7

Reactant 1

HCID 178497625HCID 178497625, compound

Product 2

HCID 178497023HCID 178497023, compoundYield 3%HCID 178497422HCID 178497422, compoundYield 70%

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
50 °C

Procedure

Following general procedure F using methyl 2‐(3‐(2,2,2‐trifluoroacetamido)propyl)benzoate (57.9 mg, 0.20 mmol), B2pin2 (101 mg, 0.40 mmol), [Ir(COD)OMe]2 (2.0 mg, 0.0030 mmol) and 1a (3.0 mg, 0.0060 mmol) in THF (1.0 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 >20:1 meta:para borylation in 100% yield. The crude product was purified by silica gel chromatography (Pet. Ether (40‐60):EtOAc (9:1‐8‐1) to give the title compound (as a 20:1 mixture of meta:para ratio, as determined by 1 H NMR) as a colourless oil (60.3 mg, 0.145 mmol, 73%).

Sources & evidence

ORD record
ord-95f9d9d54cbb4a7cbe27d6e616c6127a
Source dataset
Borylation dataset from Roche

Reaction notes

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