Trimethylsilyldiazomethane → HCID 86669289, compound

HRID 2042806Notes

Reaction equation

HRID 2042806 reaction equation
[CH3:1][Si](C=[N+]=[N-])(C)C.[Cl:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]([OH:15])=[O:14])=[C:11]([O:18][CH2:19][CH:20]([F:22])[F:21])[N:10]=1>CO.C(Cl)Cl>[CH3:1][O:14][C:13](=[O:15])[C:12]1[CH:16]=[CH:17][C:9]([Cl:8])=[N:10][C:11]=1[O:18][CH2:19][CH:20]([F:21])[F:22]

Participants

5

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 82004536HCID 82004536, compound

Product 1

HCID 86669289HCID 86669289, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

Trimethylsilyl diazomethane (2 M in hexane; 15.0 mL, 30.0 mmol) is added to a mixture of 6-chloro-2-(2,2-difluoro-ethoxy)-nicotinic acid (6.0 g, 25.3 mmol) in MeOH (50 mL) and DCM (100 mL). The reaction mixture is stirred at rt for 10 min, quenched with AcOH and concentrated. The residue is diluted with water and filtered. The filtercake is washed with water and dried at 40° C.

Workup

  1. customquenched with AcOH
  2. concentrationconcentrated
  3. additionThe residue is diluted with water
  4. filtrationfiltered
  5. washThe filtercake is washed with water
  6. customdried at 40° C.

Sources & evidence

ORD record
ord-dd8e0126a1ee4d858b9efa63586726e5
Source dataset
uspto-grants-2013_11
Patent number
US08586604B2

Reaction notes

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