HCID 178455116, compound → HCID 178431070, compound

HRID 1490787Notes

Reaction equation

HRID 1490787 reaction equation
CC(C)(C)[Si](C)(C)OCc1ccccc1CCNC(=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]>CC1(C)OB(c2ccc(CCNC(=O)C(F)(F)F)c(CO[Si](C)(C)C(C)(C)C)c2)OC1(C)C.CC1(C)OB(c2ccc(CO[Si](C)(C)C(C)(C)C)c(CCNC(=O)C(F)(F)F)c2)OC1(C)C

Participants

7

Reactant 1

HCID 178455116HCID 178455116, compound

Product 2

HCID 178431047HCID 178431047, compoundYield 6%HCID 178431070HCID 178431070, compoundYield 87%

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
70 °C

Procedure

Following general procedure F using 4k (90 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 70 °C for 20 hours. Analysis of crude 1 H NMR using internal standard 1,2‐dimethoxyethane showed ~14:1 meta:para borylation in 99% yield (these numbers include the meta/para products which have also undergone NH borylation at the higher temperature).  The crude product was purified by silica gel chromatography (10% EtOAc in Petroleum Ether 40‐60 o C) which resulted in the cleavage of the N‐ B bond of the NH‐borylation products and gave the title compound (as a 15.2:1 mixture of meta:para ratio, as determined by 1 H NMR) as a yellowish oil (113 mg, 0.23 mmol, 93%).

Sources & evidence

ORD record
ord-0af2969e26734ca8834292ad6162685c
Source dataset
Borylation dataset from Roche

Reaction notes

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