Methyl iodide → HCID 57517570, compound

HRID 510992Notes

Reaction equation

HRID 510992 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([OH:11])([CH3:10])[CH3:9])=[N:6][CH:7]=1.[H-].[Na+].[CH3:14]I>CN(C=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([O:11][CH3:14])([CH3:9])[CH3:10])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 154863922-(5-Bromopyridin-2-yl)propan-2-ol

Product 1

HCID 57517570HCID 57517570, compoundYield 108.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-(5-bromopyridin-2-yl)propan-2-ol (50 mg, 0.2 mmol, from Example 184, Step 3) was added to a mixture of NaH in mineral oil (10 mg, 0.5 mmol) in DMF (5 mL). The reaction was stirred for 30 min and the methyl iodide (30 μL, 0.5 mmol) was added and stirred for 2 hours. The reaction was partitioned between EtOAc and water. The combined organic layer was washed with brine, dried over MgSO4, filtered and concentrated to give crude product 5-bromo-2-(1-methoxy-1-methylethyl)pyridine as an oil (0.05 g, 90%). LCMS calculated for C9H13BrNO (M+H)+: m/z=230.0, 232.0. found: 230.0, 231.8.

Workup

  1. stirringstirred for 2 hours
  2. customThe reaction was partitioned between EtOAc and water
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-5e57f66d953a44c88f20c6aedadad0f1
Source dataset
uspto-grants-2015_08
Patent number
US09096600B2

Reaction notes

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