Methanol → (5-Azido-2-methyl-phenyl)-[2-chloro-4-(4-fluoro-phenylamino)-phenyl]-methanone

HRID 2067233Notes

Reaction equation

HRID 2067233 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:25])=[C:6]([C:8]([C:10]2[CH:15]=[CH:14][C:13]([NH:16][C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=3)=[CH:12][C:11]=2[Cl:24])=[O:9])[CH:7]=1.FC(F)(F)S([N:31]=[N+:32]=[N-])(=O)=O.CO.CCOC(C)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Cu+2]>[N:1]([C:2]1[CH:3]=[CH:4][C:5]([CH3:25])=[C:6]([C:8]([C:10]2[CH:15]=[CH:14][C:13]([NH:16][C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=3)=[CH:12][C:11]=2[Cl:24])=[O:9])[CH:7]=1)=[N+:31]=[N-:32]

Participants

8

Reactant 4

HCID 887MethanolHCID 10986786Methanesulfonyl azide, trifluoro-HCID 68418042(5-Amino-2-methyl-phenyl)-[2-chloro-4-(4-fluoro-phenylamino)-phenyl]-methanoneHCID 86584982Sodium bicarbonate ethyl acetate

Product 1

HCID 86605528(5-Azido-2-methyl-phenyl)-[2-chloro-4-(4-fluoro-phenylamino)-phenyl]-methanone

Reagents, catalysts & solvents 3

HCID 24463Copper sulfate pentahydrateCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a suspension of compound 429 (1.00 g, 2.82 mmol) in DCM (5.0 mL) was added a solution of copper(II) sulphate pentahydrate (35.2 mg, 0.14 mmol) in H2O (4.0 mL), and TEA (1.18 mL, 8.45 mmol). The crude trifluoromethansulfonic azide was added slowly under stirring to the reaction mixture followed by by MeOH (5 mL). After 18 h at RT the reaction mixture was poured into a mixture of EtOAc/NaHCO3(aq.). The organic phase was washed with water, brine, filtered and concentrated in vacuo to give the crude product. The crude product was purified by continuous gradient flash chromatography using EtOAc/petroleum ether (40-60) 0:100 to 25:75 as the eluent to afford the title compound as yellow solid.

Workup

  1. washThe organic phase was washed with water, brine
  2. filtrationfiltered
  3. concentrationconcentrated in vacuo
  4. customto give the crude product
  5. customThe crude product was purified by continuous gradient flash chromatography

Sources & evidence

ORD record
ord-221804f92bde4a69a8ef9a763821ec9e
Source dataset
uspto-grants-2012_10
Patent number
US08293772B2

Reaction notes

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