HCID 178497626, compound → HCID 178497423, compound

HRID 1490779Notes

Reaction equation

HRID 1490779 reaction equation
COC(=O)c1ccccc1CCNC(=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)ccc1CCNC(=O)C(F)(F)F.COC(=O)c1ccc(B2OC(C)(C)C(C)(C)O2)cc1CCNC(=O)C(F)(F)F

Participants

7

Reactant 1

HCID 178497626HCID 178497626, compound

Product 2

HCID 178497024HCID 178497024, compoundYield 5%HCID 178497423HCID 178497423, compoundYield 92%

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 4g (68.8 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 23:1 meta:para borylation in 97% yield (these numbers include a small amount of meta isomer that also underwent NH borylation). The crude product was purified by silica gel chromatography (15% EtOAc in Petroleum Ether 40‐60 o C) which resulted in the cleavage of the N‐B bond in the small amount of N‐borylated product and gave the title compound (as a 17.8:1 mixture of meta:para ratio, as determined by 1 H NMR) as an off‐white solid (97 mg, 0.24 mmol, 97%).

Sources & evidence

ORD record
ord-14e872ad54f443cab82f2c47a0e14408
Source dataset
Borylation dataset from Roche

Reaction notes

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