Trimethylsilyldiazomethane → 2-Cyclopropylamino-6-fluoro-3-nitrobenzoic acid methyl ester

HRID 243108Notes

Reaction equation

HRID 243108 reaction equation
[CH3:1][Si](C=[N+]=[N-])(C)C.[CH:8]1([NH:11][C:12]2[C:20]([N+:21]([O-:23])=[O:22])=[CH:19][CH:18]=[C:17]([F:24])[C:13]=2[C:14]([OH:16])=[O:15])[CH2:10][CH2:9]1>CO.C(Cl)Cl>[CH3:1][O:15][C:14](=[O:16])[C:13]1[C:17]([F:24])=[CH:18][CH:19]=[C:20]([N+:21]([O-:23])=[O:22])[C:12]=1[NH:11][CH:8]1[CH2:9][CH2:10]1

Participants

5

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 681570042-Cyclopropylamino-6-fluoro-3-nitrobenzoic acid

Product 1

HCID 681576262-Cyclopropylamino-6-fluoro-3-nitrobenzoic acid methyl esterYield 98%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

Trimethylsilyldiazomethane (2M in hexane, 2.6 mL, 5.21 mmol) was added dropwise to a solution of 2-cyclopropylamino-6-fluoro-3-nitrobenzoic acid (836 mg, 3.48 mmol) in MeOH (4 mL) and DCM (16 mL) at 0° C. The solution was stirred for 15 min then the volatiles were removed under reduced pressure to afford the title compound (867 mg, 98%). LCMS (Method C): RT 3.50 min [M+H]+ 255.10

Workup

  1. customthe volatiles were removed under reduced pressure

Sources & evidence

ORD record
ord-3c607660f8fe4ad09843d02fd067d33d
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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