Trimethylsilyldiazomethane → HCID 86618786, compound

HRID 2249400Notes

Reaction equation

HRID 2249400 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([C:8]2[C:13]([F:14])=[CH:12][C:11]([C:15]#[N:16])=[C:10]([O:17][CH3:18])[C:9]=2[F:19])[N:5]=[C:4]([C:20]([OH:22])=[O:21])[C:3]=1[Cl:23].[CH3:24][Si](C=[N+]=[N-])(C)C>O1CCCC1.CO>[NH2:1][C:2]1[CH:7]=[C:6]([C:8]2[C:13]([F:14])=[CH:12][C:11]([C:15]#[N:16])=[C:10]([O:17][CH3:18])[C:9]=2[F:19])[N:5]=[C:4]([C:20]([O:22][CH3:24])=[O:21])[C:3]=1[Cl:23]

Participants

5

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 86613846HCID 86613846, compound

Product 1

HCID 86618786HCID 86618786, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A slurry of 4-amino-3-chloro-6-(4-cyano-2,6-difluoro-3-methoxyphenyl)pyridine-2-carboxlic acid in tetrahydrofuran (10 mL) and methanol (3 mL) was treated with trimethylsilyldiazomethane (0.64 g, 0.28 mL of a 2M solution in hexanes) at ambient temperature. After 1 hour the reaction mixture was quenched with acetic acid (2 mL) and water (10 mL). The mixture was extracted with ethyl acetate (2×20 mL) and the combined extracts dried (Na2SO4), and concentrated. The residue was purified by chromatography (30-100% ethyl acetate in hexanes) to give 4-amino-3-chloro-6-(4-cyano-2,6-difluoro-3-methoxyphenyl)pyridine-2-carboxylic acid, methyl ester (0.083 g, 0.24 mmol): 1H NMR (CDCl3) δ 7.15 (dd, 1H), 6.85 (s, 1H), 4.98 (bs, 2H), 4.08 (d, 3h), 3.98 (s, 3H).

Workup

  1. customAfter 1 hour the reaction mixture was quenched with acetic acid (2 mL) and water (10 mL)
  2. extractionThe mixture was extracted with ethyl acetate (2×20 mL)
  3. dry with materialthe combined extracts dried (Na2SO4)
  4. concentrationconcentrated
  5. customThe residue was purified by chromatography (30-100% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-1aa724ea96b8489a87c356c92cf1a924
Source dataset
uspto-grants-2008_01
Patent number
US07314849B2

Reaction notes

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