Dimethyl Sulfoxide → HCID 89704911, compound

HRID 928935Notes

Reaction equation

HRID 928935 reaction equation
[N:1]([C:4]1[C:19]([O:20]CC2C=CC=CC=2)=[CH:18][C:7]([C:8]([O:10]CC2C=CC=CC=2)=[O:9])=[C:6]([NH:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[F:35])[C:5]=1[F:36])=[N+]=[N-].CCOCC.CS(C)=O.S1(CCCC1)(=O)=O>[Pd].[Ni].O.C(O)CC.C(O)C.CO.CN1C(=O)N(C)CCC1.CN(P(N(C)C)(N(C)C)=O)C>[NH2:1][C:4]1[C:19]([OH:20])=[CH:18][C:7]([C:8]([OH:10])=[O:9])=[C:6]([NH:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[F:35])[C:5]=1[F:36]

Participants

13

Reactant 4

HCID 679Dimethyl SulfoxideHCID 3283Diethyl EtherHCID 31347SulfolaneHCID 89704786HCID 89704786, compound

Product 1

HCID 89704911HCID 89704911, compound

Reagents, catalysts & solvents 8

HCID 935NickelCatalystHCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 887MethanolSolventHCID 962WaterSolventHCID 10311-PropanolSolventHCID 12679HexamethylphosphoramideSolventHCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-Solvent

Procedure

Benzyl 4-azido-5-(benzyloxy)-3-fluoro-2-((2-fluorophenyl)amino)benzoate can be hydrogenated catalyzed by appropriate catalyst (such as Pd/C, Pt, Ni) in the solvent (include aliphatic and aromatic hydrocarbon (such as pentane, hexane, heptane, cyclohexane, petroleum ether, petrol, gasoline, benzene, toluene, xylene), ether (such as diethyl ether, dibutyl ether, glycol dimethyl ether, 2-methoxyethyl ether, tetrahydrofuran, dioxane), ester (such as ethyl acetate, methyl acetate), amide (such as N,N-dimethylformamide, N,N-dimethylacetamide and N-methylpyrrolidin-2-one), DMSO, sulfolane, HMPA, DMPU, prefer methanol, ethanol, propan-1-ol and water) for some time (1-12 h, prefer 3-10 h). 4-Amino-3-fluoro-2-((2-fluorophenyl)amino)-5-hydroxybenzoic acid is obtained after conventional workup.

Sources & evidence

ORD record
ord-cb1c54aec0d449b68197db2c8cf826be
Source dataset
uspto-grants-2016_03
Patent number
US09290468B2

Reaction notes

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