N-Methylbenzamide → N-Methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide

HRID 1490936Notes

Reaction equation

HRID 1490936 reaction equation
CNC(=O)c1ccccc1>C1=CCCC=CCC1.C1=CCCC=CCC1.C1CCOC1.CC(C)(C)O.CC1(C)OB(B2OC(C)(C)C(C)(C)O2)OC1(C)C.C[OH2+].C[OH2+].O=c1ccc2cccc(-c3ccc(-c4ccccn4)nc3)c2[nH]1.[Ir].[Ir].[K]>CNC(=O)c1cccc(B2OC(C)(C)C(C)(C)O2)c1

Participants

7

Reactant 1

HCID 11954N-Methylbenzamide

Product 1

HCID 53217108N-Methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamideYield 15%

Reagents, catalysts & solvents 5

HCID 2733548Bis(pinacolato)diboraneReagentHCID 1646813858-([2,2'-bipyridin]-5-yl)quinolin-2(1H)-oneReagentHCID 76001521Bis(1,5-cyclooctadiene)dimethoxydiiridiumCatalystHCID 86639980Potassium tert-butoxideCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

In an argon filled glove box, a 5.0 mL wheaton microreactor was charged with [Ir(cod)(OMe)]2 (1.98 mg, 1.5 mol%), L1 ligand (2.1 mg, 3.5 mol%), B2pin2 (50.8 mg, 1.0 equiv.), KOtBu (1.0 mg, 4.5 mol%) and dry THF (1.0 mL). The reaction mixture was stirred for 2 minutes at room temperature. To this mixture, N-methylbenzamide (27.0 mg, 0.2 mmol) was added. The microreactor was capped with a teflon pressure cap and placed into pre-heated aluminum block at 80 oC. After 12 h (judged by GC/MS, conv: 33%), THF was removed under reduced pressure and chromatographic separation with silica gel (15% ethyl acetate in hexane as eluent) gave the metaborylated product 2b (7.8 mg, 15%) as white solid.

Sources & evidence

ORD record
ord-1c8a8a8e2ca64eeea9380cbf12ba2bc5
Source dataset
Borylation dataset from Roche

Reaction notes

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