Methanesulfonic Acid → HCID 89704789, compound

HRID 928937Notes

Reaction equation

HRID 928937 reaction equation
[F:1][C:2]1[C:7]2[N:8]=[CH:9][O:10][C:6]=2[CH:5]=[C:4]([C:11]([OH:13])=[O:12])[C:3]=1[NH:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[F:21].C1C(=O)N([I:29])C(=O)C1.FC(F)(F)C(O)=O.FC(F)(F)S(O)(=O)=O.CS(O)(=O)=O.S1(CCCC1)(=O)=O>CN(C)C(=O)C.CN(C)C=O.CN1C(=O)N(C)CCC1.CN(P(N(C)C)(N(C)C)=O)C.CS(C)=O.CCOCC.C(O)(=O)C.C(O)=O>[F:1][C:2]1[C:7]2[N:8]=[CH:9][O:10][C:6]=2[CH:5]=[C:4]([C:11]([OH:13])=[O:12])[C:3]=1[NH:14][C:15]1[CH:20]=[CH:19][C:18]([I:29])=[CH:17][C:16]=1[F:21]

Participants

15

Reactant 6

HCID 6395Methanesulfonic AcidHCID 6422Trifluoroacetic acidHCID 31347SulfolaneHCID 62406Trifluoromethanesulfonic acidHCID 120273N-IodosuccinimideHCID 89704884HCID 89704884, compound

Product 1

HCID 89704789HCID 89704789, compound

Reagents, catalysts & solvents 8

HCID 176Acetic AcidSolventHCID 284Formic AcidSolventHCID 679Dimethyl SulfoxideSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolventHCID 12679HexamethylphosphoramideSolventHCID 31374DimethylacetamideSolventHCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-Solvent

Procedure

4-Fluoro-5-((2-fluorophenyl)amino)benzo[d]oxazole-6-carboxylic acid can be reacted with halogenations reagent (such as NIS) in the presence of acid (such as trifluoroacetic acid, trifluoromethanesulfonic acid, methanesulfonic acid, formic acid, acetic acid) at ambient temperature in appropriate solvent (include aliphatic and aromatic hydrocarbon (such as pentane, hexane, heptane, cyclohexane, petroleum ether, petrol, gasoline, benzene, toluene, xylene), aliphatic and aromatic halo-hydrocarbon (such as dichloromethane, 1,2-dichloroethane, chloroform, phenixin, chlorobenzene, o-dichlorobenzene), ether (such as diethyl ether, dibutyl ether, glycol dimethyl ether, 2-methoxyethyl ether, tetrahydrofuran, dioxane), ketone (such as acetone, methyl ethyl ketone, methyl isopropyl ketone, methyl isobutyl ketone), ester (such as ethyl acetate, methyl acetate), nitrile (such as acetonitrile, propiononitrile), amide (such as N,N-dimethylformamide, N,N-dimethylacetamide and N-methylpyrrolidin-2-one), DMSO, sulfolane, HMPA, DMPU, prefer N,N-dimethylformamide and N,N-dimethylacetamide) for some time (1-12 h, prefer 3-10 h). 4-Fluoro-5-((2-fluoro-4-iodophenyl)amino)benzo[d]oxazole-6-carboxylic acid is obtained after conventional workup.

Sources & evidence

ORD record
ord-fc4c43e7fbe84fadaf36d4f108c1c734
Source dataset
uspto-grants-2016_03
Patent number
US09290468B2

Reaction notes

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