HCID 86713119, compound → HCID 86713109, compound

HRID 1399447Notes

Reaction equation

HRID 1399447 reaction equation
[Cl:1][C:2]1[CH:21]=[C:20]([F:22])[C:19]([N+:23]([O-])=O)=[CH:18][C:3]=1[C:4]([NH:6][CH2:7][C:8]([O:10]CC1C=CC=CC=1)=[O:9])=[O:5]>CCOC(C)=O.[Pd]>[NH2:23][C:19]1[C:20]([F:22])=[CH:21][C:2]([Cl:1])=[C:3]([CH:18]=1)[C:4]([NH:6][CH2:7][C:8]([OH:10])=[O:9])=[O:5]

Participants

4

Reactant 1

HCID 86713119HCID 86713119, compound

Product 1

HCID 86713109HCID 86713109, compoundYield 67.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of benzyl 2-(2-chloro-4-fluoro-5-nitrobenzamido)acetate (190 mg) in EtOAc (10 mL) was added Pd/C (200 mg) and stirred under the atmosphere of H2 gas at 60° C. for 20 min. Work-up of the reaction mixture as described in example 1 gave the product as an off-white solid (86 mg, 67%), mp 225-227° C. (decomposed). 1H NMR (400 MHz, DMSO-d6): δ 8.52 (1H, br s), 7.19 (1H, d, J=10.8 Hz), 6.89 (1H, d, J=9.2 Hz), 5.48 (2H, br s), 3.86 (2H, d, J=3.6 Hz); LC-MS (negative ion mode): m/z 245, 247 (M−H)−.

Sources & evidence

ORD record
ord-4e09d639a5b94057a030bf9cfc40efee
Source dataset
uspto-grants-2014_12
Patent number
US08906344B2

Reaction notes

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