Methyl iodide → HCID 178499139, compound

HRID 1507623Notes

Reaction equation

HRID 1507623 reaction equation
[CH3:1][O:2][C:3]([C:5]1[NH:6][C:7](=[S:17])[NH:8][C:9]=1[C:10]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=1)=[O:4].[C:18]([O-])([O-])=O.[K+].[K+].CI>CO>[CH3:1][O:2][C:3]([C:5]1[N:6]=[C:7]([S:17][CH3:18])[NH:8][C:9]=1[C:10]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=1)=[O:4]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 13290681HCID 13290681, compound

Product 1

HCID 178499139HCID 178499139, compoundYield 100.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a stirred solution of compound 7 (18 g, 71.0 mmol) in MeOH (200 mL) was added K2CO3 (12.0 g, 85.0 mmol), followed by the dropwise addition of a solution of MeI (8.9 mL, 143 mmol) in MeOH (200 mL) at rt. The resulting mixture was stirred at rt for 2 h and then concentrated under reduced pressure. The residue was treated with water (200 mL) and extracted with ethyl acetate (150 mL×3). The combined extracts were washed with brine (50 mL×2), dried over anhydrous MgSO4, filtered, and evaporated to afford product 8 (19.0 g, 100%) as a white solid. ESI MS m/z 267.2 (M+H)+.

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionThe residue was treated with water (200 mL)
  3. extractionextracted with ethyl acetate (150 mL×3)
  4. washThe combined extracts were washed with brine (50 mL×2)
  5. dry with materialdried over anhydrous MgSO4
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-3b10d91509664f7d8bfbcb46a6b1d983
Source dataset
uspto-grants-2015_12
Patent number
US09221805B2

Reaction notes

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