Ethyl Acetate → 3-Methyl-2-(tributylstannyl)pyridine

HRID 2175952Notes

Reaction equation

HRID 2175952 reaction equation
Br[C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][N:3]=1.[Li]CCCC.[CH2:14]([Sn:18](Cl)([CH2:23][CH2:24][CH2:25][CH3:26])[CH2:19][CH2:20][CH2:21][CH3:22])[CH2:15][CH2:16][CH3:17].CCOC(C)=O>C1COCC1>[CH3:8][C:7]1[C:2]([Sn:18]([CH2:19][CH2:20][CH2:21][CH3:22])([CH2:23][CH2:24][CH2:25][CH3:26])[CH2:14][CH2:15][CH2:16][CH3:17])=[N:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 15096Tributyltin ChlorideHCID 2208322-Bromo-3-methylpyridineHCID 178418339Butyllithium

Product 1

HCID 164270983-Methyl-2-(tributylstannyl)pyridineYield 27%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 2-bromo-3-methylpyridine (1.3 mL, 11.7 mmol) in THF (35 mL) at −78° C. was added n-BuLi (2.5 M in hexanes, 5.6 mL, 14 mmol). After 30 min, tri-n-butyltin chloride (3.8 mL, 14 mmol) was added. After 1 h at −78° C., the reaction was allowed to warm to rt. EtOAc was added and the reaction mixture was washed with 10% aq KF. The organic layer was dried (MgSO4). Purification via silica gel chromatography (0-15% EtOAc in heptane) gave the title compound (1.2 g, 27%). MS (ESI) mass calcd. for C18H33NSn, 382.2; m/z found 384.0 [M+H]+.

Workup

  1. waitAfter 1 h at −78° C.
  2. washthe reaction mixture was washed with 10% aq KF
  3. dry with materialThe organic layer was dried (MgSO4)
  4. customPurification via silica gel chromatography (0-15% EtOAc in heptane)

Sources & evidence

ORD record
ord-64601938b724457b9965be867182847d
Source dataset
uspto-grants-2015_06
Patent number
US09062078B2

Reaction notes

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