Water → 5-chloro-7-fluoro-1-methyl-2-pyridin-3-yl-1H-indole

HRID 1661635Notes

Reaction equation

HRID 1661635 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([F:11])[CH:10]=1)[NH:7][C:6]([C:12]1[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=1)=[CH:5]2.[H-].[Na+].I[CH3:21].O>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([F:11])[CH:10]=1)[N:7]([CH3:21])[C:6]([C:12]1[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=1)=[CH:5]2

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 595346575-chloro-7-fluoro-2-pyridin-3-yl-1H-indole

Product 1

HCID 582155765-chloro-7-fluoro-1-methyl-2-pyridin-3-yl-1H-indole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-chloro-7-fluoro-2-pyridin-3-yl-1H-indole (Example 86, 276 mg, 1.12 mmol) in DMF (4 mL) is added 60% sodium hydride in mineral oil (120 mg, 3.0 mmol) and the suspension is stirred for 30 min. Iodomethane (213 mg, 1.5 mmol) is then added to the reaction mixture and stirred at ambient temperature for 1 h. Water (2 mL) is added to quench the reaction. The mixture is filtered and purified by HPLC using Xbridge C18 with a gradient of acetonitrile in 0.1% NH4OH to afford 5-chloro-7-fluoro-1-methyl-2-pyridin-3-yl-1H-indole. MS (ESI) m/z 261 (M+H)+.

Workup

  1. stirringstirred at ambient temperature for 1 h
  2. customto quench
  3. customthe reaction
  4. filtrationThe mixture is filtered
  5. custompurified by HPLC

Sources & evidence

ORD record
ord-42aa36411c00462e9194c3a276044504
Source dataset
uspto-grants-2011_10
Patent number
US08030334B2

Reaction notes

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