Methanol → HCID 59424693, compound

HRID 1711017Notes

Reaction equation

HRID 1711017 reaction equation
[F:1][C:2]1[CH:17]=[C:16]([N+:18]([O-:20])=[O:19])[CH:15]=[CH:14][C:3]=1[O:4][C:5]1[C:6]2[NH:13][CH:12]=[CH:11][C:7]=2[N:8]=[CH:9][N:10]=1.[H-].[Na+].[CH3:23]O.CN([CH:28]=[O:29])C>>[F:1][C:2]1[CH:17]=[C:16]([N+:18]([O-:20])=[O:19])[CH:15]=[CH:14][C:3]=1[O:4][C:5]1[C:6]2[N:13]([CH2:23][O:29][CH3:28])[CH:12]=[CH:11][C:7]=2[N:8]=[CH:9][N:10]=1

Participants

5

Reactant 4

HCID 887MethanolHCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 59424565HCID 59424565, compound

Product 1

HCID 59424693HCID 59424693, compoundYield 49%

Conditions

Temperature
0 °C

Procedure

To a suspension of 243 (150 mg, 0.547 mmol in DMF (6 mL) was added NaH (66 mg, 1.64 mmol), and the reaction mixture was stirred at 0° C. for 1 hour. Chloromethyl methyl ester (132 mg, 1.641 mmol) was added drop wise and the mixture was stirred at room temperature over night. MeOH (2 mL) was added and the mixture was stirred for an additional hour and partitioned between EtOAc and water. The organic phase was collected, dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford title compound 244 (86 mg, 49% yield, crude) as an orange solid. MS (m/z): 319.1 (M+1).

Workup

  1. stirringthe mixture was stirred at room temperature over night
  2. stirringthe mixture was stirred for an additional hour
  3. custompartitioned between EtOAc and water
  4. customThe organic phase was collected
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c7d99344478c4b5cbbd0c27d42694bb1
Source dataset
uspto-grants-2010_09
Patent number
US07790729B2

Reaction notes

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