HCID 178453188, compound → HCID 178453130, compound

HRID 1490771Notes

Reaction equation

HRID 1490771 reaction equation
CC(C)(C)OC(=O)NCCc1ccccc1C(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]>CC(C)(C)OC(=O)NCCc1cc(B2OC(C)(C)C(C)(C)O2)ccc1C(F)(F)F.CC(C)(C)OC(=O)NCCc1ccc(B2OC(C)(C)C(C)(C)O2)cc1C(F)(F)F

Participants

7

Reactant 1

HCID 178453188HCID 178453188, compound

Product 2

HCID 178453130HCID 178453130, compoundYield 78%HCID 178453140HCID 178453140, compoundYield 9%

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 4c (72.3 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). Stirred in vial at 50 °C for 20 hours. Analysis of crude 1 H NMR using internal standard 1,2‐dimethoxyethane showed 8.3:1 meta:para borylation in 86% yield. The crude product was purified by silica gel chromatography (10% EtOAc in Petroleum Ether 40‐60 o C) gave the title compound (as a 8.8:1 mixture of meta:para ratio, as determined by 1 H NMR) as a white solid (91 mg, 0.22 mmol, 87%).

Sources & evidence

ORD record
ord-8560e57c774e4b10a8c1ed3c01a1d144
Source dataset
Borylation dataset from Roche

Reaction notes

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