Methyl iodide → 1-(tert-Butyl-dimethyl-silanyl)-5-methyl-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine

HRID 1994187Notes

Reaction equation

HRID 1994187 reaction equation
Br[C:2]1[CH:3]=[C:4]2[CH2:10][CH2:9][N:8]([Si:11]([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12])[C:5]2=[N:6][CH:7]=1.[Li][C:19](C)(C)C.CCCCC.CI>CCOCC>[C:14]([Si:11]([CH3:13])([CH3:12])[N:8]1[C:5]2=[N:6][CH:7]=[C:2]([CH3:19])[CH:3]=[C:4]2[CH2:10][CH2:9]1)([CH3:17])([CH3:16])[CH3:15]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 8003PentaneHCID 587309295-Bromo-1-(tert-butyl-dimethyl-silanyl)-2,3-dihydro-1H-pyrrolo[2,3-b]pyridineHCID 178418306HCID 178418306, compound

Product 1

HCID 575977571-(tert-Butyl-dimethyl-silanyl)-5-methyl-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a stirred and cooled (−78° C.) solution of bromide 4 (0.20 g, 0.64 mmol) in Et2O (2.5 mL) was added dropwise a 1.5 M solution of tert-BuLi in pentane (0.89 mL, 1.34 mmol). After 38 min MeI (0.1 mL, 1.61 mmol) was added dropwise and the mixture allowed to gradually warm to r.t. After 12 h the mixture was partitioned between CHCl3 and saturated aqueous NaHCO3 solution. The aqueous layer was extracted with CHCl3 (2×). The combined organic extracts were dried (MgSO4), and concentrated to afford 7 as a yellow oily residue, which was used directly in the next step without purification.

Workup

  1. customAfter 12 h the mixture was partitioned between CHCl3 and saturated aqueous NaHCO3 solution
  2. extractionThe aqueous layer was extracted with CHCl3 (2×)
  3. dry with materialThe combined organic extracts were dried (MgSO4)
  4. concentrationconcentrated
  5. customto afford 7 as a yellow oily residue, which
  6. customwas used directly in the next step without purification

Sources & evidence

ORD record
ord-ee2f884a9f034b4ca9c8ccafb02e9bd6
Source dataset
uspto-grants-2010_01
Patent number
US07652137B2

Reaction notes

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