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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1490950Generated: October 30, 2026

Benzamide, 2-methoxy-N,N-bis(1-methylethyl)- → HCID 178488282, compound

https://huagongshe.com/reaction/1490950

Reaction equation

Participants

RoleNameHCIDCharge
ReactantBenzamide, 2-methoxy-N,N-bis(1-methylethyl)-HCID 698398—
ReagentBis(pinacolato)diboraneHCID 2733548—
Reagent8-([2,2'-bipyridin]-5-yl)quinolin-2(1H)-oneHCID 164681385—
CatalystBis(1,5-cyclooctadiene)dimethoxydiiridiumHCID 76001521—
CatalystPotassium tert-butoxideHCID 86639980—
SolventTetrahydrofuranHCID 8028—
ProductHCID 178488282HCID 17848828294%

Reaction Conditions

Temperature80 °C

Reaction Steps

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,N-diisopropyl-2-methoxybenzamide (47.1 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. The reaction mixture was stirred for 12 h. After completion (judged by GC/MS), THF was removed under reduced pressure and chromatographic separation with silica gel (20% ethyl acetate in hexane as eluent) gave the meta-borylated product 6b (67.9 mg, 94%) as white solid.

Provenance & Evidence

DOI10.1002/anie.201809929
Source datasetBorylation dataset from Roche
ORD IDord-dfa9f272026e4fa791a7a13a0d7f89fc
Source noteBorylation dataset from Roche