Methyl iodide → 4-Chloro-5-methyl-1-[tri(propan-2-yl)silyl]-1H-pyrrolo[2,3-b]pyridine

HRID 1821234Notes

Reaction equation

HRID 1821234 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8]([Si:11]([CH:18]([CH3:20])[CH3:19])([CH:15]([CH3:17])[CH3:16])[CH:12]([CH3:14])[CH3:13])[CH:9]=[CH:10][C:3]=12.[Li][CH:22](CC)C.CI>O1CCCC1>[Cl:1][C:2]1[C:7]([CH3:22])=[CH:6][N:5]=[C:4]2[N:8]([Si:11]([CH:15]([CH3:17])[CH3:16])([CH:18]([CH3:20])[CH3:19])[CH:12]([CH3:13])[CH3:14])[CH:9]=[CH:10][C:3]=12

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 114382724-Chloro-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridineHCID 178418400CID 53628100

Product 1

HCID 242292764-Chloro-5-methyl-1-[tri(propan-2-yl)silyl]-1H-pyrrolo[2,3-b]pyridineYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a cold −78° C. solution of 4-chloro-1-[tris(1-methylethyl)silyl]-1H-pyrrolo[2,3-b]pyridine (3.24 mmol, prepared as described in Tetrahedron Lett. 2004, 45, 2317-2319), in dry tetrahydrofuran (22 mL) was added 1.4M sec-BuLi in hexanes (7.12 mmol) dropwise over ˜5 min. After 30 min, methyliodide (10.5 mmol) was added. After 45 min, the reaction mixture was quenched with saturated aqueous ammonium chloride (25 mL) and diluted with ethyl acetate (25 mL). The extracts were dried over sodium sulfate, filtered, concentrated under reduced pressure and the residue was purified by silica gel chromatography (100% hexanes) to give the title product as a white solid (86%). ESMS [M+H]+: 323.2

Workup

  1. waitAfter 45 min
  2. customthe reaction mixture was quenched with saturated aqueous ammonium chloride (25 mL)
  3. additiondiluted with ethyl acetate (25 mL)
  4. dry with materialThe extracts were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customthe residue was purified by silica gel chromatography (100% hexanes)

Sources & evidence

ORD record
ord-ad6b42cb9267408b9f087a24115fa310
Source dataset
uspto-grants-2009_10
Patent number
US07605266B2

Reaction notes

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