2,6-Dimethoxypyridine → 2,6-Dimethoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine

HRID 1490565Notes

Reaction equation

HRID 1490565 reaction equation
COc1cccc(OC)n1>C1=CCCC=CCC1.C1=CCCC=CCC1.CC1(C)OB(B2OC(C)(C)C(C)(C)O2)OC1(C)C.COC1CCCC1.C[OH2+].C[OH2+].[Ir].[Ir].c1ccc(N2B(B3Nc4ccccc4N3c3ccccn3)Nc3ccccc32)nc1>COc1cc(B2OC(C)(C)C(C)(C)O2)cc(OC)n1

Participants

6

Reactant 1

HCID 803782,6-Dimethoxypyridine

Product 1

HCID 467394422,6-Dimethoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridineYield 69%

Reagents, catalysts & solvents 4

HCID 2733548Bis(pinacolato)diboraneReagentHCID 1223807993-pyridin-2-yl-2-(3-pyridin-2-yl-1H-1,3,2-benzodiazaborol-2-yl)-1H-1,3,2-benzodiazaboroleReagentHCID 76001521Bis(1,5-cyclooctadiene)dimethoxydiiridiumCatalystHCID 138539Cyclopentyl methyl etherSolvent

Conditions

Temperature
100 °C

Procedure

The general procedure A was followed using 2,6-dimethoxypyridine (69.6 mg, 0.5 mmol) and B2pin2 (126.9 mg, 0.5 mmol, 1.0 eq.) as starting material. The resulting mixture was allowed to stir 16 hours at 100 oC. 5x was obtained as white solid (91.5 mg, 69%) after purification by silica gel flash chromatography (Acetone/PE=1:5 v/v). m.p.: 97-99 oC.

Sources & evidence

ORD record
ord-1e52b4ddd38c4c05a7343b3e9b602f01
Source dataset
Borylation dataset from Roche

Reaction notes

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