Hexane → 2,3-Dimethyl-6-mehylthiopyrrolo[2,3-b]pyridine

HRID 1756104Notes

Reaction equation

HRID 1756104 reaction equation
Br[C:2]1[N:7]=[C:6]2[NH:8][C:9]([CH3:12])=[C:10]([CH3:11])[C:5]2=[CH:4][CH:3]=1.[Li]CCCC.CCCCCC.[CH3:24][S:25]SC>C1COCC1.O>[CH3:12][C:9]1[NH:8][C:6]2=[N:7][C:2]([S:25][CH3:24])=[CH:3][CH:4]=[C:5]2[C:10]=1[CH3:11]

Participants

7

Reactant 4

HCID 8058HexaneHCID 12232Dimethyl DisulfideHCID 193925846-Bromo-2,3-dimethyl-pyrrolo[2,3-b]pyridineHCID 178418339Butyllithium

Product 1

HCID 193926102,3-Dimethyl-6-mehylthiopyrrolo[2,3-b]pyridineYield 83.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A deaerated solution of 6-bromo-2,3-dimethyl-pyrrolo [2,3-b]pyridine (225 mg, 1.0 mmol) in 25 ml dry THF was cooled to -78° C. and treated with 1.6M n-BuLi in hexane (1,5 ml, 2.4 mmol). The reaction mixture was brought to 0° C. and the lithiate trapped with dimethyl disulfide (444 μl, 5 mmol). After reacting for 5 min 1.5 ml H2O was added and the THF evaporated. The residue was taken up in 100 ml CH2Cl2 and washed with 50 ml 5% NaHCO3, 50 ml 2M HCl (reextracted twice with 25 ml CH2Cl2), and 50 ml 5% NaHCO3. The organic layer was dried over MgSO4 and evaporated leaving 160 mg (83%) pure 2,3-dimethyl-6-methylthio-pyrrolo[2,3-b]pyridine.

Workup

  1. customwas brought to 0° C.
  2. customthe THF evaporated
  3. washwashed with 50 ml 5% NaHCO3, 50 ml 2M HCl (
  4. dry with materialThe organic layer was dried over MgSO4
  5. customevaporated

Sources & evidence

ORD record
ord-6cce0143eac54158bbc55ff0518b0a82
Source dataset
uspto-grants-1995_08
Patent number
US05439917

Reaction notes

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