3-Methyl-2-(tributylstannyl)pyridine → Methyl 3,6'-dimethyl-[2,3'-bipyridine]-2'-carboxylate

HRID 2175953Notes

Reaction equation

HRID 2175953 reaction equation
Br[C:2]1[C:3]([C:9]([O:11][CH3:12])=[O:10])=[N:4][C:5]([CH3:8])=[CH:6][CH:7]=1.[CH3:13][C:14]1[C:15]([Sn](CCCC)(CCCC)CCCC)=[N:16][CH:17]=[CH:18][CH:19]=1>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:13][C:14]1[C:15]([C:2]2[C:3]([C:9]([O:11][CH3:12])=[O:10])=[N:4][C:5]([CH3:8])=[CH:6][CH:7]=2)=[N:16][CH:17]=[CH:18][CH:19]=1

Participants

5

Reactant 2

HCID 164270983-Methyl-2-(tributylstannyl)pyridineHCID 90404668Methyl 3-bromo-6-methylpyridine-2-carboxylate

Product 1

HCID 90412135Methyl 3,6'-dimethyl-[2,3'-bipyridine]-2'-carboxylateYield 18.9%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
150 °C

Procedure

To the title compound of step B (509 mg, 2.2 mmol) and the title compound of step C (1.1 g, 2.9 mmol) in PhCH3 (6.6 mL) was added Pd(PPh3)4 (225 mg, 0.2 mmol). The reaction was degassed with N2 and heated at 150° C. for 1.5 h using microwave reactor. The reaction was cooled to rt, diluted with H2O and extracted with EtOAc. The organic layer was dried (MgSO4). Purification via silica gel chromatography (0-100% EtOAc in heptane) gave the title compound (101 mg, 18%). MS (ESI) mass calcd. for C14H14N2O2, 242.3; m/z found 243 [M+H]+.

Workup

  1. customThe reaction was degassed with N2
  2. temperatureThe reaction was cooled to rt
  3. additiondiluted with H2O
  4. extractionextracted with EtOAc
  5. dry with materialThe organic layer was dried (MgSO4)
  6. customPurification via silica gel chromatography (0-100% EtOAc in heptane)

Sources & evidence

ORD record
ord-8354ce1514984632a8d94ed947c04494
Source dataset
uspto-grants-2015_06
Patent number
US09062078B2

Reaction notes

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