Methyl cyanoacetate → Methyl-5-amino-3-(2-fluorophenyl)isoxazol-4-carboxylate

HRID 2276418

Reaction equation

HRID 2276418 reaction equation
[F:1][C:2]1[CH:11]=[CH:10][CH:9]=[CH:8][C:3]=1[C:4](Cl)=[N:5][OH:6].[CH3:12][O:13][C:14](=[O:18])[CH2:15][C:16]#[N:17].C[O-].[Na+]>CO>[CH3:12][O:13][C:14]([C:15]1[C:4]([C:3]2[CH:8]=[CH:9][CH:10]=[CH:11][C:2]=2[F:1])=[N:5][O:6][C:16]=1[NH2:17])=[O:18]

Participants

5

Reactant 3

HCID 7747Methyl cyanoacetateHCID 37581182-fluoro-N-hydroxybenzenecarboximidoyl chlorideHCID 10942334Sodium Methoxide

Product 1

HCID 70982071Methyl-5-amino-3-(2-fluorophenyl)isoxazol-4-carboxylateYield 76%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a similar manner as described in Preparation Example 17, by using methanol (160 mL), 2-fluoro-N-hydroxybenzimidoyl chloride (8.00 g, 46.09 mmol), methylcyanoacetate (5.94 g, 59.92 mmol) and sodium methoxide (4.98 g, 92.18 mmol), a white solid required compound (8.23 g, 34.82 mmol, 76%) was obtained.

Workup

  1. customIn a similar manner as described in Preparation Example 17

Sources & evidence

ORD record
ord-a0ef1b62ed22474da3b5d2b6daf8464d
Source dataset
uspto-grants-2015_09
Patent number
US09132126B2

Linked notes

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