Reaction #50919

ord-2afadabeeba04b919f5703d1f49b9196

Reaction equation

O=C([O-])[O-].[Na+].[Na+]
sodium carbonate
CCCN(C(=O)Nc1ccc(I)cc1)N(C(=O)OC(C)(C)C)c1cccc(C#N)c1
405
CCCN(C(=O)Nc1ccc(I)cc1)N(C(=O)OC(C)(C)C)c1cccc(C#N)c1
tert-Butyl 2-(3-cyanophenyl)-3-(4-iodophenylaminocarbonyl)-3-propylcarbazate
CSc1ccccc1B(O)O
2-(methylthio)-phenylboronic acid
→
CCCN(C(=O)Nc1ccc(-c2ccccc2SC)cc1)N(C(=O)OC(C)(C)C)c1cccc(C#N)c1
409
Yield 85.9%
CCCN(C(=O)Nc1ccc(-c2ccccc2SC)cc1)N(C(=O)OC(C)(C)C)c1cccc(C#N)c1
tert-Butyl 2-(3-cyanophenyl)-3-(2′-methylthiobiphenyl-4-ylaminocarbonyl)-3-propylcarbazate
Yield 85.9%

Reactants

O=C([O-])[O-].[Na+].[Na+]
sodium carbonate
CCCN(C(=O)Nc1ccc(I)cc1)N(C(=O)OC(C)(C)C)c1cccc(C#N)c1
405
CCCN(C(=O)Nc1ccc(I)cc1)N(C(=O)OC(C)(C)C)c1cccc(C#N)c1
tert-Butyl 2-(3-cyanophenyl)-3-(4-iodophenylaminocarbonyl)-3-propylcarbazate
CSc1ccccc1B(O)O
2-(methylthio)-phenylboronic acid

Reagents

[Cl][Pd][Cl].[Fe+2].c1ccc(P(c2ccccc2)[c-]2cccc2)cc1.c1ccc(P(c2ccccc2)[c-]2cccc2)cc1
PdCl2(dppf)

Solvents

COCCOC
ethylene glycol dimethyl ether

Conditions

Temperature
110°CELSIUS
Detailed conditions
See reaction.notes.procedure_details.

Procedure

1.5 g (2.883 mmol) of 405 and 0.968 g (5.766 mmol) of 2-(methylthio)-phenylboronic acid are dissolved in 100 ml of ethylene glycol dimethyl ether, treated with 63 mg (0.086 mmol) of PdCl2(dppf) and 20.0 ml of 2N sodium carbonate solution and then stirred at 110° C. under a nitrogen atmosphere for 3 h. After customary work-up, 1.28 g (75.9%) of 409 are thus obtained as crystals having a melting point of 184-185° C.; MS(FAB)=517.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US06849626B2uspto-grants-2005_02