Sodium hydride → Methyl 6-chloro-3-(3-(trifluoromethyl)phenylamino)benzo[d]isoxazole-7-carboxylate

HRID 1695537Notes

Reaction equation

HRID 1695537 reaction equation
[Cl:1][C:2]1[C:7]([C:8]([O:10][CH3:11])=[O:9])=[C:6](F)[C:5]([C:13](=[N:25][OH:26])[NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[CH:16]=2)=[CH:4][CH:3]=1.[H-].[Na+]>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:13]([NH:14][C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[CH:16]=3)=[N:25][O:26][C:6]=2[C:7]=1[C:8]([O:10][CH3:11])=[O:9]

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 178498354HCID 178498354, compound

Product 1

HCID 67276645Methyl 6-chloro-3-(3-(trifluoromethyl)phenylamino)benzo[d]isoxazole-7-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of methyl 6-chloro-2-fluoro-3-(N′-hydroxy-N-(3-(trifluoromethyl)phenyl)carbamimidoyl)benzoate (1.1 g, 2.8 mmol) in DMF cooled to 0° C. was added NaH (0.136 g, 3.39 mmol) portionwise. The resulting orange solution was stirred at 0° C. for 2 h. The reaction was partitioned between EtOAc (50 ml), brine (30 mL), and water (20 mL). The aqueous layer was back exacted with EtOAc (3×20 mL) and the combined EtOAc layer was dried (Na2SO4) and concentrated to provide the title compound as a crude product.

Workup

  1. customThe reaction was partitioned between EtOAc (50 ml), brine (30 mL), and water (20 mL)
  2. dry with materialthe combined EtOAc layer was dried (Na2SO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-b45cd3a15881444aaa5891b61d51013a
Source dataset
uspto-grants-2012_04
Patent number
US08163742B2

Reaction notes

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